Bicyclic compounds as pest control agents

ABSTRACT

The present application relates to novel bicyclic compounds, to their use for controlling animal pests and to processes and intermediates for their preparation.

The present application relates to novel bicyclic compounds, tocompositions comprising these compounds, to their use for controllinganimal pests and to processes and intermediates for their preparation.

Recently, bicyclic compounds having insecticidal properties have beendisclosed (WO 2015/038503 A1).

WO 2010/078408 A1 describes the preparation and pharmaceutical use ofRaf kinase inhibitors and WO 2013/259064 A1 describes the synthesis ofanti-HIV agents and their use for the treatment of HIV infections, whichcompounds contain, inter alia, an N-substituted2H-pyrazolo[3,4-b]pyridin-1-yl fragment. WO 2010/056999 describes thepreparation of parasiticides containing an N-substituted2H-pyrazolo[3,4-b]pyridin-1-yl fragment.

Modern crop protection compositions have to meet many demands, forexample in relation to extent, persistence and spectrum of their actionand possible use. Questions of toxicity and of combinability with otheractive compounds or formulation auxiliaries play a role, as does thequestion of the expense that the synthesis of an active compoundrequires. In addition, resistances can occur. For all these reasonsalone, the search for novel crop protection compositions cannot beconsidered complete, and there is a constant need for novel compoundshaving improved properties compared to the known compounds, at least inrelation to individual aspects.

It was an object of the present invention to provide compounds whichwiden the spectrum of the pesticides under various aspects.

The object, and further objects which are not stated explicitly but canbe discerned or derived from the connections discussed herein, areachieved by compounds of the formula (I)

in which

-   -   A represents an A radical from the group consisting of (A-a) to        (A-f)

-   -   -   where the broken line represents the bond to the nitrogen            atom of the bicyclic system of the formula (I) and

    -   G¹ represents N or C—B¹,

    -   B¹ represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and        in each case optionally substituted cycloalkyl and cycloalkenyl,

    -   B² represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and        in each case optionally substituted cycloalkyl and cycloalkenyl,

    -   T represents oxygen or an electron pair,

    -   R² a) represents a radical from the group consisting of (B-1) to        (B-36)

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² b) represents a D radical from the group consisting of (D-1)        to (D-3)

-   -   where the broken line denotes the bond to the carbon atom of the        bicyclic system of the formula (I), or    -   R² c) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² d) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² e) represents an F radical from the group consisting of (F-1)        to (F-11)

-   -   where the broken line denotes the bond to the carbon atom of the        bicyclic system of the formula (I), or    -   R² f) represents a radical from the group consisting of        haloalkyl, carboxyl and amino,        -   in which    -   G² represents hydrogen or a radical from the group consisting of        halogen, nitro, amino, cyano, alkylamino, haloalkylamino,        dialkylamino, alkyl, haloalkyl, alkoxycarbonylalkyl, saturated        or unsaturated cycloalkyl which is optionally substituted and        optionally interrupted by one or more heteroatoms,        cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated        alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl,        alkylsulfonylalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl,        alkoxy(alkylsulfanyl)alkyl, alkoxy(alkylsulfinyl)alkyl,        alkoxy(alkylsulfonyl)alkyl, bis(alkylsulfanyl)alkyl,        bis(haloalkylsulfanyl)alkyl, bis(hydroxyalkylsulfanyl)alkyl,        alkoxycarbonyl, alkoxycarbonylalkyl,        alpha-hydroxyiminoalkoxycarbonylalkyl,        alpha-alkoxyiminoalkoxycarbonylalkyl, C(X²)NR³R⁴, NR⁶R⁷,        alkylthio, alkylsulfinyl, alkylsulfonyl, the heterocyclyl        radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl,        oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl,        dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide,        oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide,        oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide,        oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl,        dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl,        dihydrooxazinyl and pyrazolinonyl (which for their part may be        substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl        (which for its part may be substituted by halogen, cyano, nitro,        alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl        N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl,        furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl,        thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl        (which for their part may be substituted by halogen, nitro,        alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio,        alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals        triazolylalkyl, pyridylalkyl, pyrimidylalkyl and        oxadiazolylalkyl (which for their part may be substituted by        halogen and alkyl),        -   or    -   G² represents a C radical from the group consisting of (C-1) to        (C-9)

-   -   -   where the broken line denotes the bond to the radicals (B-1)            to (B-36),

    -   X represents oxygen or sulfur,

    -   X¹ represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and        haloalkoxy,

    -   X² represents oxygen, sulfur, NR⁵ or NOH,

    -   L represents oxygen or sulfur,

    -   V-Z represents R²⁴CH—CHR²⁵ or R²⁴C═CR²⁵,

    -   n represents 1 or 2,

    -   m represents 1, 2, 3 or 4,

    -   R represents NR¹⁸R¹⁹, or represents an in each case optionally        substituted radical from the group consisting of alkyl, alkenyl,        alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S(O)-alkyl,        alkyl-S(O)₂-alkyl, R¹⁸—CO-alkyl, NR¹⁸R¹⁹—CO-alkyl, cycloalkyl,        cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl,        heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and        hetarylalkyl,

    -   R³ represents hydrogen or alkyl,

    -   R⁴ represents a radical from the group consisting of hydrogen,        alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl,        cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl,        alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl,        alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl,

    -   R⁵ represents a radical from the group consisting of hydrogen,        alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl,        cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl,        alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and        hetarylalkyl, or

    -   R³ and R⁴ together with the nitrogen atom to which they are        attached form a ring which may contain one or more further        heteroatoms from the group consisting of nitrogen, oxygen and        sulfur, or

    -   R³ and R⁵ together with the nitrogen atoms to which they are        attached form a ring,

    -   R⁶ represents hydrogen or alkyl,

    -   R⁷ represents a radical from the group consisting of hydrogen,        alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl,        cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl,        alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl,        alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl,        arylalkyl and hetarylalkyl, or

    -   R⁶ and R⁷ together with the nitrogen atom to which they are        attached form a ring which may contain one or more further        heteroatoms from the group consisting of nitrogen, oxygen and        sulfur,

    -   R⁸ represents a radical from the group consisting of hydrogen,        alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl,        alkoxyalkyl, in each case optionally halogen-substituted        alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted        alkoxycarbonyl, optionally halogen-, alkyl-, alkoxy-, haloalkyl-        and cyano-substituted cycloalkylcarbonyl, or a cation, or an        optionally alkyl- or arylalkyl-substituted ammonium ion,

    -   R⁹ represents a radical from the group consisting of in each        case optionally substituted alkyl, alkenyl and alkynyl, in each        case optionally substituted cycloalkyl, cycloalkylalkyl and        cycloalkenyl, in which the rings may contain at least one        heteroatom from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen, in each case optionally substituted aryl, heteroaryl,        arylalkyl and heteroarylalkyl and an optionally substituted        amino group,

    -   R⁸ and R⁹ in the radicals (C-1) and (F-1) may also form,        together with the N—S(O)n group to which they are attached, a        saturated or unsaturated and optionally substituted 4- to        8-membered ring which may contain one or more further        heteroatoms from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen and/or at least one carbonyl group,

    -   R¹⁰ represents hydrogen or alkyl,

    -   R⁸ and R¹⁰ in the radicals (C-2) and (F-2), together with the        nitrogen atoms to which they are attached, may also be a        saturated or unsaturated and optionally substituted 4- to        8-membered ring which may contain at least one further        heteroatom from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen and/or at least one carbonyl group,

    -   R⁹ and R¹⁰ in the radicals (C-2) and (F-2), together with the        N—S(O)n group to which they are attached, may also form a        saturated or unsaturated and optionally substituted 4- to        8-membered ring which may contain one or more further        heteroatoms from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen and/or at least one carbonyl group,

    -   R¹¹ represents an in each case optionally substituted radical        from the group consisting of alkyl, alkenyl, alkynyl, alkoxy,        alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy,        cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio,        phenoxy, , phenylthio, benzyloxy, benzylthio, heteroaryloxy,        heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,

    -   R¹² represents an in each case optionally substituted radical        from the group consisting of alkyl, alkenyl, alkynyl, alkoxy,        alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy,        cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio,        phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy,        heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,

    -   R¹¹ and R¹² in the radicals (C-3) and (F-3), together with the        phosphorus atom to which they are attached, may also form a        saturated or unsaturated and optionally substituted 5- to        7-membered ring which may contain one or two heteroatoms from        the group consisting of oxygen (where oxygen atoms must not be        directly adjacent to one another) and sulfur,

    -   R¹³ represents an in each case optionally substituted radical        from the group consisting of alkyl, alkenyl, alkynyl, phenyl and        phenylalkyl,

    -   R¹⁴ represents an in each case optionally substituted radical        from the group consisting of alkyl, alkenyl, alkynyl, phenyl and        phenylalkyl,

    -   R¹⁵ represents a radical from the group consisting of in each        case optionally substituted alkyl, alkenyl and alkynyl, in each        case optionally substituted cycloalkyl, cycloalkylalkyl and        cycloalkenyl, in which the rings may contain at least one        heteroatom from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen, in each case optionally substituted aryl, heteroaryl,        arylalkyl and heteroarylalkyl and an optionally substituted        amino group,

    -   R⁸ and R¹⁵ in the radicals (C-6) and (F-6), together with the        N—S(O)n group to which they are attached, may also form a        saturated or unsaturated and optionally substituted 4- to        8-membered ring which may contain one or more further        heteroatoms from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen and/or at least one carbonyl group,

    -   R¹⁶ represents a radical from the group consisting of hydrogen,        in each case optionally substituted alkyl, alkoxy, alkenyl and        alkynyl, in each case optionally substituted cycloalkyl,        cycloalkylalkyl and cycloalkenyl, in which the rings may contain        at least one heteroatom from the group consisting of sulfur,        oxygen (where oxygen atoms must not be directly adjacent to one        another) and nitrogen, in each case optionally substituted aryl,        heteroaryl, arylalkyl and heteroarylalkyl and an optionally        substituted amino group,

    -   R⁸ and R¹⁶ in the radicals (C-7) and (F-7), together with the        nitrogen atom to which they are attached, may also form a        saturated or unsaturated and optionally substituted 4- to        8-membered ring which may contain one or more further        heteroatoms from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen and/or at least one carbonyl group,

    -   R¹⁷ represents a radical from the group consisting of in each        case optionally substituted alkyl, alkoxy, alkenyl and alkynyl,        in each case optionally substituted cycloalkyl, cycloalkylalkyl        and cycloalkenyl, in which the rings may contain at least one        heteroatom from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen, in each case optionally substituted aryl, heteroaryl,        arylalkyl and heteroarylalkyl and an optionally substituted        amino group,

    -   R⁸ and R¹⁷ in the radicals (C-8) and (F-8), together with the        N—C(X) group to which they are attached, may also form a        saturated or unsaturated and optionally substituted 4- to        8-membered ring which may contain one or more further        heteroatoms from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen and/or at least one carbonyl group,

    -   R¹⁸ represents a radical from the group consisting of hydrogen,        hydroxy, in each case optionally substituted alkyl, alkoxy,        alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl,        alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and        alkynyl, in each case optionally substituted cycloalkyl,        cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which        the rings may contain at least one heteroatom from the group        consisting of sulfur, oxygen (where oxygen atoms must not be        directly adjacent to one another) and nitrogen, in each case        optionally substituted aryl, arylalkyl, heteroaryl and        heteroarylalkyl and an optionally substituted amino group,

    -   R¹⁹ represents a radical from the group consisting of hydrogen,        represents an alkali metal or alkaline earth metal ion or        represents an ammonium ion which is optionally mono- to        tetrasubstituted by C₁-C₄-alkyl or represents an in each case        optionally halogen- or cyano-substituted alkyl, alkoxy,        alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl,        alkylsulfonylalkyl radical,

    -   Y¹ and Y² independently of one another represent C═O or S(O)₂,

    -   Y³ represents a radical from the group consisting of hydrogen,        halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy        and NR²⁰R²¹,

    -   W represents a radical from the group consisting of O, S, SO and        SO₂,

    -   R²² represents a radical from the group consisting of alkyl,        optionally halogen-, carbamoyl-, thiocarbamoyl- or        cyano-substituted cycloalkyl, haloalkyl, alkoxy, haloalkoxy,        alkoxyalkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl,        haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl,        alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl,        alkylthioalkyloxy, alkylsulfinylalkyloxy, alkylsulfonylalkyloxy,        haloalkylthioalkyl, halogenalkylsulfinylalkyl,        haloalkylsulfonylalkyl, alkylthioalkenyl, alkylsulfinylalkenyl,        alkylsulfonylalkenyl, alkenylthioalkyl, alkenylsulfinylalkyl,        alkenylsulfonylalkyl, alkylcarbonylalkyl,        haloalkylcarbonylalkyl, alkoxyalkyl, haloalkoxyalkyl,        alkoxycarbonylalkyl, haloalkoxycarbonylalkyl,        alkylaminosulfonyl, di(alkylamino)sulfonyl, or,        -   in the case R²=d),

    -   R²² also represents optionally substituted aryl or represents an        E radical from the group consisting of E-1 to E-51

-   -   R²⁰ represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, amino, hydroxy and in each case        optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl,        cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy,        alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy,        cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy,        alkylamino, alkenylamino, alkynylamino, cycloalkylamino,        alkylthio, haloalkylthio, alkenylthio, alkynylthio,        cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl,        alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl,        alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl,        alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino,        alkenylcarbonylamino, alkynylcarbonylamino,        cycloalkylcarbonylamino, alkoxycarbonylamino,        alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl        and heteroaryloxy, where the substituents are independently of        one another selected from halogen, cyano, nitro, hydroxy, amino,        alkyl and haloalkyl,    -   R²¹ represents a radical from the group consisting of hydrogen,        alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl,        cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl,        haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl        and haloalkylsulfonyl,    -   R²³ represents a radical from the group consisting of hydrogen,        alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy,        alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl,        alkenylthioalkyl, cyanoalkyl, alkoxyalkyl and    -   R²⁴ represents hydrogen or an in each case optionally        substituted radical from the group consisting of alkyl, alkenyl,        alkynyl, phenyl and phenylalkyl and    -   R²⁵ represents hydrogen or an in each case optionally        substituted radical from the group consisting of alkyl, alkenyl,        alkynyl, phenyl and phenylalkyl,    -   R²⁷ represents hydrogen or alkyl and    -   R²⁶ represents a radical from the group consisting of hydrogen,        alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl,        alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl,        alkylsulfonylalkyl and cyanoalkyl.

It has been additionally found that the compounds of the formula (I)have good efficacy as pesticides, for example against arthropods andespecially insects, and additionally generally have very goodcompatibility with plants, especially crop plants, and/or havefavourable toxicological and/or favourable environmentally relevantproperties.

Range of preference (1): Preference is given to compounds of the formula(I) in which

-   -   A represents a radical from the group consisting of (A-a), (A-b)        and (A-f)

-   -   -   where the broken line represents the bond to the nitrogen            atom of the bicyclic system of the formula (I) and

    -   G¹ represents N or C—B¹,

    -   B¹ represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl,

    -   B² represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl,

    -   T represents oxygen or an electron pair,

    -   R² a) represents a radical from the group consisting of (B-1) to        (B-36)

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² b) represents a D radical from the group consisting of (D-1)        to (D-3)

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or        -   R² c) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or        -   R² d) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or        -   R² e) represents a radical from the group consisting of            (F-1), (F-8), (F-10) and (F-11)

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I),

    -   R² f) represents a radical from the group consisting of        C₁-C₆-haloalkyl, carboxyl and amino,

    -   in which

    -   G² represents hydrogen or represents a radical from the group        consisting of halogen, nitro, amino, cyano, C₁-C₄-alkylamino,        halo-C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)-amino, C₁-C₄-alkyl,        halo-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl, halogenated C₁-C₄-alkoxy-C₁-C₄-alkyl,        bis(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        bis(halo-C₁-C₄-alkoxy)-C₁-C₄-alkyl,        C₁-C₄-alkoxy-(C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxy-(C₁-C₄-alkylsulfinyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxy-(C₁-C₄-alkylsulfonyl)-C₁-C₄-alkyl,        bis(C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        bis(halo-C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        bis(hydroxy-C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        alpha-hydroxyimino-C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        alpha-C₁-C₄-alkoxyimino-C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C(X²)NR³R⁴, NR⁶R⁷, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-alkylsulfonyl, the heterocyclyl radicals dioxanyl,        dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl,        oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl,        dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl        oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl        dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide,        morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl,        dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and        pyrazolinonyl (which for their part may be substituted by        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and        C₁-C₄-alkoxy-C₁-C₄-alkyl), phenyl (which for its part may be        substituted by halogen, cyano, nitro, C₁-C₄-alkyl and        halo-C₁-C₄-alkyl), the heteroaryl radicals pyridyl, pyridyl        N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl,        furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl,        thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl        (which for their part may be substituted by halogen, nitro,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio,        C₁-C₄-alkylthio-C₁-C₄-alkyl and C₃-C₆-cycloalkyl) and the        heteroaryl-C₁-C₄-alkyl radicals triazolyl-C₁-C₄-alkyl,        pyridyl-C₁-C₄-alkyl, pyrimidyl-C₁-C₄-alkyl and        oxadiazolyl-C₁-C₄-alkyl (which for their part may be substituted        by halogen and C₁-C₄-alkyl),        -   or

    -   G² represents a C radical from the group consisting of (C-1) and        (C-6) to (C-9)

-   -   -   where the broken line denotes the bond to the radicals (B-1)            to (B-36),

    -   X represents oxygen or sulfur,

    -   X¹ represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy,

    -   X² represents oxygen, sulfur, NR⁵ or NOH,

    -   V-Z represents R²⁴CH—CHR²⁵ or R²⁴C═CR²⁵,

    -   n represents 1 or 2,

    -   R represents NR¹⁸R¹⁹ or represents C₁-C₆-alkyl, C₃-C₆-alkenyl,        C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,        C₁-C₆-alkyl-S—C₁-C₄-alkyl, C₁-C₆-alkyl-S(O)—C₁-C₄-alkyl,        C₁-C₆-alkyl-S(O)₂—C₁-C₄-alkyl, each of which is optionally        substituted by halogen, oxygen (leads to C═O) or cyano,        represents R¹⁸—CO—C₁-C₄-alkyl, represents        NR¹⁸R¹⁹—CO—C₁-C₄-alkyl, represents C₃-C₆-cycloalkyl which is        optionally mono- or disubstituted by oxygen (leads to C═O),        C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl,        represents C₃-C₈-cycloalkenyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkenyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        heterocyclyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        heterocyclyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, or        represents phenyl, phenyl-C₁-C₄-alkyl, hetaryl and        hetaryl-C₁-C₄-alkyl, each of which is optionally mono- to        trisubstituted by halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

    -   R³ represents hydrogen or C₁-C₆-alkyl,

    -   R⁴ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        aryl, aryl-C₁-C₄-alkyl and hetaryl-C₁-C₄-alkyl,

    -   R⁵ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        aryl, aryl-C₁-C₄-alkyl and hetaryl-C₁-C₄-alkyl, or

    -   R³ and R⁴ together with the nitrogen atom to which they are        attached form a 4- to 7-membered ring which may contain one or        two further heteroatoms from the group consisting of nitrogen,        oxygen and sulfur (where oxygen and sulfur atoms must not be        directly adjacent to one another),

    -   R⁶ represents hydrogen or C₁-C₄-alkyl,

    -   R⁷ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₄-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy,        halo-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, aryl, aryl-C₁-C₄-alkyl and        hetaryl-C₁-C₄-alkyl, or

    -   R⁶ and R⁷ together with the nitrogen atom to which they are        attached form a 4- to 7-membered ring which may contain one or        two further heteroatoms from the group consisting of nitrogen,        oxygen and sulfur (where oxygen and sulfur atoms must not be        directly adjacent to one another),

    -   R⁸ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, in        each case optionally halogen-substituted C₁-C₆-alkylcarbonyl and        C₁-C₆-alkylsulfonyl, optionally halogen-substituted        C₁-C₆-alkoxycarbonyl, optionally halogen-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- and cyano-substituted        C₃-C₆-cycloalkylcarbonyl, or represents a cation or an        optionally C₁-C₆-alkyl- or aryl-C₁-C₆-alkyl-substituted ammonium        ion,

    -   R⁹ represents a radical from the group consisting of in each        case optionally halogen-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulfinyl-,        C₁-C₆-haloalkylsulfinyl-, C₁-C₆-alkylsulfonyl- and        C₁-C₆-haloalkylsulfonyl-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl        and C₂-C₆-alkynyl, in each case optionally halogen-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy- or        C₁-C₆-haloalkoxy-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl and C₃-C₆-cycloalkenyl, in which        one ring member may be replaced by a heteroatom from the group        consisting of sulfur, oxygen (where oxygen atoms must not be        directly adjacent to one another) and nitrogen (and here in        particular represent

-   -   -   where the arrow in each case marks the bond to the sulfur            atom in the (C-1) radical and in the (F-1) radical), in each            case optionally halogen-, cyano- (including in the alkyl            moiety), nitro-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,            C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,            C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-,            C₁-C₆-alkylsulfinyl-, C₁-C₆-haloalkylsulfinyl-,            C₁-C₆-alkylsulfonyl-, C₁-C₆-haloalkylsulfonyl-, amino-,            C₁-C₆-alkylamino-, di(C₁-C₆-alkyl)amino-,            C₁-C₆-alkylcarbonylamino-, C₁-C₆-alkoxycarbonylamino-,            C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₁-C₆-haloalkoxy-C₁-C₆-alky            C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,            C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,            C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted aryl,            heteroaryl, aryl-C₁-C₆-alkyl, heteroaryl-C₁-C₆-alkyl, or is            NR′R″ in which R′ and R″ are independently a radical from            the group consisting of hydrogen, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,            C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl, or

    -   R⁸ and R⁹ in the radical (C-1) and in the radical (F-1),        together with the N—S(O)_(n) group to which they are attached,        may also form a saturated or unsaturated and optionally        halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may        contain one or two heteroatoms from the group consisting of        sulfur, oxygen (where oxygen atoms must not be directly adjacent        to one another) and nitrogen and/or at least one and preferably        one carbonyl group; in particular, R⁸ and R⁹ together with the        N—S(O)_(n) group to which they are attached may represent a        radical from the group consisting of

-   -   -   (in which the arrow in each case marks the bond to the C(X)            group)

    -   R¹⁵ represents a radical from the group consisting of in each        case optionally methyl-, cyano-, carbamoyl-substituted        C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, in each case        optionally methyl-, trifluoromethyl-, halogen-, cyano- or        carbamoyl-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₂-alkyl and C₃-C₆-cycloalkenyl, in which        the rings may contain at least one heteroatom from the group        consisting of sulfur, oxygen (where oxygen atoms must not be        directly adjacent to one another) and nitrogen, in each case        optionally C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-haloalkylsulfinyl-, C₁-C₄-haloalkylsulfonyl-,        C₁-C₄-alkylamino-, di-(C₁-C₄-alkyl)-amino-, halogen-, nitro- or        cyano-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₂-alkyl and an optionally C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkyl-C₁-C₄-alkoxycarbonyl- or        C₁-C₄-alkylsulfonyl-substituted amino group,

    -   R⁸ and R¹⁵ in the radical (C-6), together with the N—S(O)n group        to which they are attached, may also form a saturated or        unsaturated and optionally substituted 4- to 8-membered ring        which may contain one or two further heteroatoms from the group        consisting of sulfur, oxygen (where oxygen and sulfur atoms must        not be directly adjacent to one another) and nitrogen and/or at        least one carbonyl group,

    -   R¹⁶ represents a radical from the group consisting of hydrogen,        in each case optionally methyl-, cyano-, carbamoyl- or        carboxyl-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₄-alkenyl        and C₂-C₄-alkynyl, in each case optionally halogen-, cyano-,        nitro-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-,        C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulfinyl-,        C₁-C₆-haloalkylsulfonyl-, C₁-C₆-alkylsulfonyl-,        C₁-C₆-haloalkylsulfonyl-, amino-, C₁-C₆-alkylamino-,        di-(C₁-C₆-alkyl)amino-, C₁-C₆-alkylcarbonylamino-,        C₁-C₆-alkoxycarbonylamino-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl- or        C₁-C₆-alkylcarbonyl-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl and C₃-C₆-cycloalkenyl in which the        rings may contain at least one heteroatom from the group        consisting of sulfur, oxygen (where oxygen atoms must not be        directly adjacent to one another) and nitrogen, in each case        optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-,        C₁-C₆-alkylsulfinyl-, C₁-C₆-haloalkylsulfinyl-,        C₁-C₆-alkylsulfonyl-, C₁-C₆-haloalkylsulfonyl-, amino-,        C₁-C₆-alkylamino-, di-(C₁-C₆-alkyl)amino-,        C₁-C₆-alkylcarbonylamino-, C₁-C₆-alkoxycarbonylamino-,        C₂-C₆-alkenyl-, C₂-C₆-alkynyl- or        C₁-C₆-alkylcarbonyl-substituted aryl, heteroaryl,        aryl-C₁-C₂-alkyl and heteroaryl-C₁-C₂-alkyl and an optionally        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-,        C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulfinyl-,        C₁-C₆-haloalkylsulfinyl-, C₁-C₆-alkylsulfonyl-,        C₁-C₆-haloalkylsulfonyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl- or        C₁-C₆-alkylcarbonyl-substituted amino group,

    -   R¹⁷ represents a radical from the group consisting of in each        case optionally halogen-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulfinyl-,        C₁-C₆-haloalkylsulfinyl-, C₁-C₆-alkylsulfonyl- or        C₁-C₆-haloalkylsulfonyl-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₂-C₆-alkenyl and C₂-C₆-alkynyl, in each case optionally        halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, or        C₁-C₆-haloalkoxy-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl and C₃-C₆-cycloalkenyl,        N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl,        N-thiomorpholinyl 1-oxide, N-thiomorpholinyl 1,1-dioxide,        N-piperazinyl, N-1-methylpiperazinyl or        N-2-oxo-1-methylpiperazinyl, in each case optionally halogen-,        cyano- (also in the alkyl moiety), nitro-, C₁-C₆-alkyl-,        C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-,        C₁-C₆-alkylsulfinyl-, C₁-C₆-haloalkylsulfinyl-,        C₁-C₆-alkylsulfonyl-, C₁-C₆-haloalkylsulfonyl-, amino-,        C₁-C₆-alkylamino-, di(C₁-C₆-alkyl)amino-,        C₁-C₆-alkylcarbonylamino-, C₁-C₆-alkoxycarbonylamino-,        C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₁-C₆-haloalkoxy-C₁-C₆-alkyl-,        C₂-C₆-alkenyl-, C₂-C₆-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₆-alkyl-,        C₁-C₆-alkylcarbonyl-, C₁-C₆-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl,        heteroaryl-C₁-C₆-alkyl or represents NR′R″ in which R′ and R″        independently of one another each represent a radical from the        group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl and        C₁-C₆-alkoxycarbonyl,

    -   R⁸ and R¹⁷ in the radical (C-8) and in the radical (F-8),        together with the N—C(X) group to which they are attached, may        also form a saturated or unsaturated and optionally halogen-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may        contain one or two further heteroatoms from the group consisting        of sulfur, oxygen (where oxygen atoms must not be directly        adjacent to one another) and nitrogen and/or one carbonyl group;        in particular, R⁸ and R¹⁷ together with the N—C(X) group to        which they are attached may represent a radical from the group        consisting of

-   -   -   (where the arrow in each case denotes the bond to the sulfur            atom in the radical (C-8) and in the radical (F-8)),

    -   R¹⁸ represents a radical from the group consisting of hydrogen,        hydroxy, of C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₄-alkyl,        C₁-C₆-alkyl-S—C₁-C₄-alkyl, C₁-C₆-alkyl-S(O)—C₁-C₄-alkyl,        C₁-C₆-alkyl-S(O)₂—C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl,        C₁-C₆-alkoxycarbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,        C₃-C₆-cycloalkyl-C₁-C₃-alkyl, C₃-C₆-cycloalkenyl-C₁-C₃-alkyl,        heterocyclyl, heterocyclyl-C₁-C₃-alkyl, each of which is        optionally mono- or polysubstituted by halogen or mono- or        disubstituted by cyano, and phenyl, phenyl-C₁-C₃-alkyl, hetaryl        and hetaryl-C₁-C₃-alkyl, each of which is optionally mono- to        tetrasubstituted by C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, halogen or cyano,

    -   R¹⁹ represents hydrogen, an alkali or alkaline earth metal ion,        or represents an ammonium ion which is optionally mono- to        tetrasubstituted by C₁-C₄-alkyl, or represents a radical from        the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkyl-S—C₁-C₄-alkyl,        C₁-C₄-alkyl-S(O)—C₁-C₄-alkyl and C₁-C₄-alkyl-S(O)₂—C₁-C₄-alkyl,        each of which is optionally mono- or polysubstituted by halogen        or mono- or disubstituted by cyano,

    -   Y³ represents a radical from the group consisting of hydrogen,        halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and NR²⁰R²¹,

    -   W represents a radical from the group consisting of O, S, SO and        SO₂,

    -   R²² represents a radical from the group consisting of        C₁-C₆-alkyl, optionally halogen-, carbamoyl-, thiocarbamoyl- or        cyano-substituted C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyloxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,        C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyloxy,        C₁-C₄-alkylsulfinyl-C₁-C₄-alkyloxy,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyloxy,        C₁-C₄-haloalkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfinyl-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfonyl-C₂-C₄-alkenyl,        C₂-C₄-alkenylthio-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfinyl-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylcarbonyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylaminosulfonyl,        di(C₁-C₄-alkyl)aminosulfonyl,        -   in the case R²=d),

    -   R²² also represents optionally halogen-, cyano-, nitro-, amino-,        hydroxy-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₂-C₆-alkenyl-,        C₂-C₆-alkynyl-, C₃-C₆-cycloalkyl-, C₃-C₆-alkenyloxy-,        C₃-C₆-alkynyloxy-, C₁-C₆-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₆-alkoxycarbonyloxy-, C₁-C₆-alkylamino-,        C₃-C₆-alkenylamino-, C₃-C₆-alkynylamino-,        C₃-C₆-cycloalkylamino-, C₁-C₆-alkylthio-, C₁-C₄-alkylsulfinyl-,        C₁-C₄-alkylsulfonyl-, C₃-C₆-alkenylthio-, C₃-C₆-alkynylthio-,        C₃-C₆-cycloalkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-haloalkylsulfinyl-, C₁-C₄-haloalkylsulfonyl-,        C₁-C₆-alkylcarbonyl-, aminocarbonyl-, C₁-C₆-alkylaminocarbonyl-,        di-(C₁-C₆)-alkylaminocarbonyl-, C₁-C₆-alkylcarbonylamino-,        C₁-C₆-alkylamino- or C₁-C₆-dialkylamino-substituted aryl or        represents an E radical from the group consisting of E-1 to E-51

-   -   R²⁰ represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, amino, hydroxy, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy , C₃-C₆-alkenyloxy,        C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyloxy, C₁-C₆-alkylcarbonyloxy,        C₂-C₆-alkenylcarbonyloxy, C₂-C₆-alkynylcarbonyloxy,        C₃-C₆-cycloalkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy,        C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylamino, C₃-C₆-alkenylamino,        C₃-C₆-alkynylamino, C₃-C₆-cycloalkylamino, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio,        C₃-C₆-cycloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,        C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,        C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,        di-(C₁-C₆)-alkylaminocarbonyl, aminothiocarbonyl,        C₁-C₆-alkylaminosulfonyl, C₁-C₆-alkylsulfonylamino,        C₁-C₆-alkylcarbonylamino, C₁-C₆-alkylthiocarbonylamino, of        phenyl, phenoxy, pyridinyl and pyridinyloxy, each of which is        optionally substituted by a radical from the group consisting of        halogen, cyano, nitro, amino, hydroxy, C₁-C₆-alkyl and        C₁-C₆-haloalkyl,    -   R²¹ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl,        C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,        C₁-C₆-haloalkylcarbonyl, C₂-C₆-haloalkenylcarbonyl,        C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylsulfonyl and C₁-C₆-haloalkylsulfonyl,    -   R²³ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,        C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyloxy,        C₁-C₄-alkylthio-C₁-C₄-alkyl, C₂-C₄-alkenylthio-C₁-C₄-alkyl,        cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    -   R²⁴ represents hydrogen or represents an in each case optionally        halogen- or cyano-substituted radical from the group consisting        of C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl and        phenyl-C₁-C₂-alkyl,    -   R²⁵ represents hydrogen or represents an in each case optionally        halogen- or cyano-substituted radical from the group consisting        of C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl and        phenyl-C₁-C₂-alkyl,    -   R²⁷ represents hydrogen or C₁-C₄-alkyl and    -   R²⁶ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl,        C₁-C₄-alkylsulfonyl-C₁-C₂-alkyl and cyano-C₁-C₄-alkyl.

Range of preference (2): Particular preference is given to compounds ofthe formula (I) in which

-   -   A represents a radical from the group consisting of (A-a), (A-b)        and (A-f)

-   -   -   where the broken line represents the bond to the nitrogen            atom of the bicyclic system of the formula (I),

    -   G¹ represents N or C—B¹,

    -   B¹ represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl,

    -   B² represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl,

    -   T represents oxygen or an electron pair,

    -   R² a) represents a B radical from the group consisting of

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² b) represents a radical from the group consisting of (D-1) to        (D-3)

-   -   where the broken line denotes the bond to the carbon atom of the        bicyclic system of the formula (I), or    -   R² c) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² d) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² e) represents an F radical from the group consisting of        (F-1), (F-8) and (F-10)

-   -   -   where the broken line represents the bond to the carbon atom            in the formula (I) or

    -   R² f) represents a radical from the group consisting of        C₁-C₆-haloalkyl, carboxyl and amino,

    -   in which

    -   G² represents hydrogen or a radical from the group consisting of        halogen, nitro, amino, cyano, C₁-C₄-alkylamino,        halo-C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, halo-C₁-C₄-alkyl,        C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        halogenated C₁-C₄-alkoxy-C₁-C₄-alkyl,        bis(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        bis(halo-C₁-C₄-alkoxy)-C₁-C₄-alkyl,        C₁-C₄-alkoxy-(C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxy-(C₁-C₄-alkylsulfinyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxy-(C₁-C₄-alkylsulfonyl)-C₁-C₄-alkyl,        bis(C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        bis(halo-C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        bis(hydroxy-C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C(X²)NR³R⁴, NR⁶R⁷, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-alkylsulfonyl, the heterocyclyl radicals dioxanyl,        dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl,        oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl,        dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl        oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl        dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide,        morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl,        dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and        pyrazolinonyl (which for their part may be substituted by        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy and        C₁-C₄-alkoxy-C₁-C₄-alkyl), phenyl (which for its part may be        substituted by halogen, cyano, nitro, C₁-C₄-alkyl and        halo-C₁-C₄-alkyl), the heteroaryl radicals pyridyl, pyridyl        N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl,        furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl,        thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl        (which for their part may be substituted by halogen, nitro,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio,        C₁-C₄-alkylthio-C₁-C₄-alkyl and C₃-C₆-cyclo-C₁-C₄-alkyl) and the        heteroaryl-C₁-C₄-alkyl radicals triazolyl-C₁-C₄-alkyl,        pyridyl-C₁-C₄-alkyl, pyrimidyl-C₁-C₄-alkyl and        oxadiazolyl-C₁-C₄-alkyl (which for their part may be substituted        by halogen and C₁-C₄-alkyl),        -   or

    -   G² represents a C radical from the group consisting of (C-1),        (C-6) and (C-9)

-   -   where the broken line denotes the bond to the B radicals,    -   X represents oxygen,    -   X¹ represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, iodine, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy,    -   X² represents oxygen, sulfur, NR⁵ or NOH,    -   n represents 2,    -   R represents NR¹⁸R¹⁹ or represents C₁-C₆-alkyl, C₃-C₆-alkenyl,        C₃-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₃-alkyl,        C₁-C₄-alkyl-S—C₁-C₃-alkyl, C₁-C₄-alkyl-S(O)—C₁-C₃-alkyl,        C₁-C₄-alkyl-S(O)₂—C₁-C₃-alkyl, each of which is optionally mono-        to heptasubstituted by halogen, mono- or disubstituted by oxygen        (leads to C═O) or mono- or disubstituted by cyano, represents        R¹⁸—CO—C₁-C₂-alkyl, represents NR¹⁸R¹⁹—CO—C₁-C₂-alkyl,        represents C₃-C₆-cycloalkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₈-cycloalkenyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkenyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        heterocyclyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        heterocyclyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, or        represents phenyl, phenyl-C₁-C₄-alkyl, hetaryl and        hetaryl-C₁-C₄-alkyl, each of which is optionally mono- to        trisubstituted by halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    -   R³ represents C₁-C₄-alkyl,    -   R⁴ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and        C₁-C₄-alkylthio-C₁-C₄-alkyl,    -   R⁵ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and        C₁-C₄-alkylthio-C₁-C₄-alkyl,    -   R⁶ represents hydrogen or C₁-C₄-alkyl,    -   R⁷ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, aryl-C₁-C₄-alkyl and        hetaryl-C₁-C₄-alkyl or    -   R⁶ and R⁷ together with the nitrogen atom to which they are        attached form a 4- to 7-membered ring which may contain one or        two further heteroatoms from the group consisting of nitrogen,        oxygen and sulfur (where oxygen and sulfur atoms must not be        directly adjacent to one another),    -   R⁸ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, in        each case optionally halogen-substituted C₁-C₆-alkylcarbonyl and        C₁-C₆-alkylsulfonyl, optionally halogen-substituted        C₁-C₆-alkoxycarbonyl and optionally halogen-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- and cyano-substituted        C₃-C₆-cycloalkylcarbonyl, or represents a cation or an        optionally C₁-C₆-alkyl- or aryl-C₁-C₆-alkyl-substituted ammonium        ion,    -   R⁹ represents a radical from the group consisting of in each        case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulfinyl-,        C₁-C₄-haloalkylsulfinyl-, C₁-C₄-alkylsulfonyl- and        C₁-C₄-haloalkylsulfonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl        and C₂-C₄-alkynyl, in each case optionally halogen-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl and C₃-C₄-cycloalkenyl, in which        one or two ring members may in each case be replaced by a        heteroatom from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen (and here in particular represent

-   -   -   where the arrow in each case marks the bond to the sulfur            atom in the radical (C-1) and in the radical (F-1)), in each            case optionally halogen-, cyano- (also in the alkyl moiety),            nitro-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-,            C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,            C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulfinyl-,            C₁-C₄-haloalkylsulfinyl-, C₁-C₄-alkylsulfonyl-,            C₁-C₄-haloalkylsulfonyl-, amino-, C₁-C₄-alkylamino-,            di(C₁-C₄-alkyl)amino-, C₁-C₄-alkylcarbonylamino-,            C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,            C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-,            C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,            C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or            aminocarbonyl-substituted aryl, heteroaryl,            aryl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl or represent NR′R″            in which R′ and R″ independently of one another represent a            radical from the group consisting of hydrogen and            C₁-C₄-alkyl, or

    -   R⁸ and R⁹ in the radical (C-1) and in the radical (F-1),        together with the N—S(O)n group to which they are attached, may        also form a saturated or unsaturated and optionally halogen-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may        contain one or two heteroatoms from the group consisting of        sulfur, oxygen (where oxygen atoms must not be directly adjacent        to one another) and nitrogen and/or at least one and preferably        exactly one carbonyl group; in particular, R⁸ and R⁹ together        with the N—S(O)n group to which they are attached may represent        a radical from the group consisting of

-   -   -   (in which the arrow in each case marks the bond to the C(X)            group)

    -   R¹⁵ represents a radical from the group consisting of in each        case optionally methyl-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl        and C₂-C₆-alkynyl, in each case optionally methyl-, halogen-,        cyano- or carbamoyl-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₂-alkyl and C₃-C₆-cycloalkenyl,

    -   R⁸ and R¹⁵ in the radical (C-6), together with the N—S(O)n group        to which they are attached, may also form a saturated or        unsaturated and optionally substituted 4- to 8-membered ring        which may contain one or two further heteroatoms from the group        consisting of sulfur, oxygen (where oxygen and sulfur atoms must        not be directly adjacent to one another) and nitrogen and/or at        least one carbonyl group,

    -   R¹⁷ represents a radical from the group consisting of in each        case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulfinyl-,        C₁-C₄-haloalkylsulfinyl-, C₁-C₄-alkylsulfonyl- and        C₁-C₄-haloalkylsulfonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl        and C₂-C₄-alkynyl, in each case optionally halogen-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl and C₃-C₄-cycloalkenyl,        N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl,        N-thiomorpholinyl 1-oxide, N-thiomorpholinyl 1,1-dioxide,        N-piperazinyl, N-1-methylpiperazinyl or        N-2-oxo-1-methylpiperazinyl, in each case optionally halogen-,        cyano- (also in the alkyl moiety), nitro-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulfinyl-, C₁-C₄-haloalkylsulfinyl-,        C₁-C₄-alkylsulfonyl-, C₁-C₄-haloalkylsulfonyl-, amino-,        C₁-C₄-alkylamino-, di(C₁-C₄-alkyl)amino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₂-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl or represents NR′R″ in which R′ and R″        independently of one another represent a radical from the group        consisting of hydrogen and C₁-C₄-alkyl,

    -   R¹⁸ represents a radical from the group consisting of hydrogen,        hydroxy, of C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkyl-S—C₁-C₃-alkyl, C₁-C₄-alkyl-S(O)—C₁-C₃-alkyl,        C₁-C₄-alkyl-S(O)₂—C₁-C₃-alkyl, C₁-C₄-alkylcarbonyl,        C₁-C₄-alkoxycarbonyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₃-alkyl, heterocyclyl,        heterocyclyl-C₁-C₃-alkyl, each of which is optionally mono- or        polysubstituted by halogen or mono- or disubstituted by cyano,        and of phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl,        pyrazolyl, thienyl, furanyl, pyridinylmethyl and        thiazolylmethyl, each of which is optionally mono- to        trisubstituted by C₁-C₄-alkyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy,        C₁-C₃-haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or        cyano,

    -   R¹⁹ represents hydrogen, represents an alkali or alkaline earth        metal ion, or represents an ammonium ion which is optionally        mono- to tetrasubstituted by C₁-C₄-alkyl, or represents a        radical from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkyl-S—C₁-C₂-alkyl,        C₁-C₄-alkyl-S(O)—C₁-C₂-alkyl and C₁-C₄-alkyl-S(O)₂—C₁-C₂-alkyl,        each of which is optionally mono- or polysubstituted by halogen        or mono- or disubstituted by cyano,

    -   Y³ represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, iodine, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy,

    -   W represents a radical from the group consisting of S, SO and        SO₂,

    -   R²², if R² represents the radical c), represents a radical from        the group consisting of C₁-C₆-alkyl, optionally halogen-,        carbamoyl-, thiocarbamoyl- or cyano-substituted        C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₄-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyloxy, C₁-C₄-alkylthio,        C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyloxy,        C₁-C₄-alkylsulfinyl-C₁-C₄-alkyloxy,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyloxy,        C₁-C₄-haloalkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfinyl-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfonyl-C₂-C₄-alkenyl,        C₂-C₄-alkenylthio-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfinyl-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylcarbonyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylaminosulfonyl,        di-(C₁-C₄-alkyl)-aminosulfonyl,

    -   R²³, if R² represents the radical c), represents a radical from        the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₂-C₄-alkenylthio-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl,

    -   R²³, if R² represents the radical d) or e), represents a radical        from the group consisting of hydrogen, C₁-C₆-alkyl,        C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,        C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyloxy,        C₁-C₄-alkylthio-C₁-C₄-alkyl, C₂-C₄-alkenylthio-C₁-C₄-alkyl,        cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄alkyl,        -   or, in the case R²=d),

    -   R²² also represents optionally halogen-, cyano-, nitro-, amino-,        hydroxy-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₆-alkoxycarbonyloxy-,        C₁-C₆-alkylamino-, C₁-C₆-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulfinyl-, C₁-C₄-alkylsulfonyl-,        C₁-C₆-alkylcarbonyl-, aminocarbonyl-, C₁-C₆-alkylaminocarbonyl-,        di-(C₁-C₆-alkyl)-aminocarbonyl-,        C₁-C₆-alkylcarbonylamino-substituted phenyl or represents an E        radical from the group consisting of

-   -   R²⁷ represents hydrogen or C₁-C₄-alkyl and    -   R²⁶ represents hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl,        C₁-C₄-alkylsulfinyl-C₁-C₂-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₂-alkyl        or cyano-C₁-C₄-alkyl.

Range of preference (3): Very particular preference is given tocompounds of the formula (I) in which

-   -   A represents a radical from the group consisting of (A-a), (A-b)        and (A-f)

-   -   -   where the broken line represents the bond to the nitrogen            atom of the bicyclic system of the formula (I),

    -   G¹ represents N or C—B¹,

    -   B¹ represents a radical from the group consisting of hydrogen        and fluorine,

    -   B² represents hydrogen,

    -   T represents oxygen or an electron pair,

    -   R² represents a B radical from the group consisting of

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² b) represents a D radical from the group consisting of (D-1)        to (D-3)

-   -   where the broken line denotes the bond to the carbon atom of the        bicyclic system of the formula (I), or    -   R² c) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² d) represents a radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I), or

    -   R² e) represents an F radical from the group consisting of        (F-1), (F-8) and (F-10)

-   -   -   where the broken line represents the bond to the carbon atom            in the formula (I), or

    -   R² f) represents a radical from the group consisting of        C₁-C₆-haloalkyl, carboxyl and amino, where

    -   G² represents hydrogen or a radical from the group consisting of        halogen, nitro, amino, cyano, C₁-C₄-alkylamino,        halo-C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, halo-C₁-C₄-alkyl,        C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        halogenated C₁-C₄-alkoxy-C₁-C₄-alkyl,        bis(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        bis(halo-C₁-C₄-alkoxy)-C₁-C₄-alkyl,        C₁-C₄-alkoxy(C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxy(C₁-C₄-alkylsulfinyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxy(C₁-C₄-alkylsulfonyl)-C₁-C₄-alkyl,        bis(C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        bis(halo-C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        bis(hydroxy-C₁-C₄-alkylsulfanyl)-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C(X²)NR³R⁴, NR⁶R⁷, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl and        C₁-C₄-alkylsulfonyl,        -   or

    -   G² represents a C radical (C-1) or (C-9)

-   -   -   where the broken line denotes the bond to the B radicals,

    -   X represents oxygen,

    -   X¹ represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, cyano, methyl, ethyl,        trifluoromethyl, methoxy, ethoxy, difluoromethoxy and        trifluoromethoxy,

    -   X² represents oxygen, sulfur, NR⁵ or NOH,

    -   n represents 2,

    -   R represents NR¹⁸R¹⁹ or represents a radical from the group        consisting of C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl,        C₁-C₂-alkoxy-C₁-C₂-alkyl and C₁-C₂-alkyl-S—C₁-C₂-alkyl,        C₁-C₂-alkyl-S(O)—C₁-C₂-alkyl, C₁-C₂-alkyl-S(O)₂—C₁-C₂-alkyl,        each of which is optionally mono-, di-, tri-, tetra- or        pentasubstituted by fluorine, chlorine or mono- or disubstituted        by cyano, represents R¹⁸—CO—C₁-C₂-alkyl, represents        NR¹⁸R¹⁹—CO—C₁-C₂-alkyl, represents C₃-C₆-cycloalkyl which is        optionally mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy        or C₁-C₂-haloalkyl or by an oxygen atom (leads to C═O),        represents C₃-C₆-cycloalkenyl which is optionally mono- or        disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl or        by an oxygen atom (leads to C═O), represents        C₃-C₆-cycloalkyl-C₁-C₂-alkyl which is optionally mono- or        disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl,        represents C₃-C₆-cycloalkenyl-C₁-C₂-alkyl which is optionally        mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or        C₁-C₂-haloalkyl, represents heterocyclyl which is optionally        mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or        C₁-C₂-haloalkyl, represents heterocyclyl-C₁-C₂-alkyl which is        optionally mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy        or C₁-C₂-haloalkyl or represents phenyl, benzyl, pyridyl,        pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl,        pyridinylmethyl or thiazolylmethyl, each of which is optionally        mono- or disubstituted by fluorine, chlorine, bromine, cyano,        methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy or trifluoromethoxy,

    -   R³ represents C₁-C₄-alkyl,

    -   R⁴ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and        C₁-C₄-alkylthio-C₁-C₄-alkyl,

    -   R⁵ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and        C₁-C₄-alkylthio-C₁-C₄-alkyl,

    -   R⁶ represents hydrogen or C₁-C₄-alkyl,

    -   R⁷ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, halo-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkynyl,        C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, aryl-C₁-C₄-alkyl and        hetaryl-C₁-C₄-alkyl or

    -   R⁶ and R⁷ together with the nitrogen atom to which they are        attached form a 4- to 7-membered ring which may contain one or        two further heteroatoms from the group consisting of nitrogen,        oxygen and sulfur (where oxygen and sulfur atoms must not be        directly adjacent to one another),

    -   R⁸ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, in        each case optionally halogen-substituted C₁-C₆-alkylcarbonyl and        C₁-C₆-alkylsulfonyl, optionally halogen-substituted        C₁-C₆-alkoxycarbonyl, optionally halogen-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- and cyano-substituted        C₃-C₆-cycloalkylcarbonyl, or represents a cation or an        optionally C₁-C₆-alkyl- or aryl-C₁-C₆-alkyl-substituted ammonium        ion,

    -   R⁹ represents a radical from the group consisting of in each        case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulfinyl-,        C₁-C₄-haloalkylsulfinyl-, C₁-C₄-alkylsulfonyl- and        C₁-C₄-haloalkylsulfonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl        and C₂-C₄-alkynyl, in each case optionally halogen-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl and C₃-C₄-cycloalkenyl, in which        one or two ring members may in each case be replaced by a        heteroatom from the group consisting of sulfur, oxygen (where        oxygen atoms must not be directly adjacent to one another) and        nitrogen (and here in particular represent

-   -   -   where the arrow in each case marks the bond to the sulfur            atom in the radical (C-1) and in the radical (F-1)), in each            case optionally halogen-, cyano- (also in the alkyl moiety),            nitro-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-,            C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,            C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulfinyl-,            C₁-C₄-haloalkylsulfinyl-, C₁-C₄-alkylsulfonyl-,            C₁-C₄-haloalkylsulfonyl-, amino-, C₁-C₄-alkylamino-,            di(C₁-C₄-alkyl)amino-, C₁-C₄-alkylcarbonylamino-,            C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,            C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-,            C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,            C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or            aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl            and heteroaryl-C₁-C₄-alkyl or represent NR′R″ in which R′            and R″ independently of one another represent a radical from            the group consisting of hydrogen and C₁-C₄-alkyl,

    -   R⁸ and R⁹ in the radical (C-1) and in the radical (F-1),        together with the N—S(O)n group to which they are attached, may        also form a saturated or unsaturated and optionally halogen-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may        contain one or two heteroatoms from the group consisting of        sulfur, oxygen (where oxygen atoms must not be directly adjacent        to one another) and nitrogen and/or at least one and preferably        one carbonyl group; in particular, R⁸ and R⁹ together with the        N—S(O)n group to which they are attached may represent a radical        from the group consisting of

-   -   -   (in which the arrow in each case marks the bond to the C(X)            group),

    -   R¹⁷ represents a radical from the group consisting of in each        case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulfinyl-,        C₁-C₄-haloalkylsulfinyl-, C₁-C₄-alkylsulfonyl- and        C₁-C₄-haloalkylsulfonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl        and C₂-C₄-alkynyl, in each case optionally halogen-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl and C₃-C₄-cycloalkenyl,        N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl,        N-thiomorpholinyl 1-oxide, N-thiomorpholinyl 1,1-dioxide,        N-piperazinyl, N-1-methylpiperazinyl and        N-2-oxo-1-methylpiperazinyl, in each case optionally halogen-,        cyano- (also in the alkyl moiety), nitro-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulfinyl-, C₁-C₄-haloalkylsulfinyl-,        C₁-C₄-alkylsulfonyl-, C₁-C₄-haloalkylsulfonyl-, amino-,        C₁-C₄-alkylamino-, di-(C₁-C₄-alkyl)amino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₂-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl or represents NR′R″ in which R′ and R″        independently of one another represent a radical from the group        consisting of hydrogen and C₁-C₄-alkyl,

    -   W represents a radical from the group consisting of S, SO and        SO₂,

    -   Y³ represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, cyano, methyl, ethyl,        trifluoromethyl, methoxy, ethoxy, difluoromethoxy and        trifluoromethoxy,

    -   R¹⁸ represents a radical from the group consisting of hydrogen,        hydroxy, of C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkyl-S—C₁-C₂-alkyl, C₁-C₄-alkyl-S(O)—C₁-C₂-alkyl,        C₁-C₄-alkyl-S(O)₂—C₁-C₂-alkyl, C₁-C₄-alkylcarbonyl,        C₁-C₄-alkoxycarbonyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₃-alkyl, heterocyclyl and        heterocyclyl-C₁-C₃-alkyl, each of which is optionally mono-,        di-, tri-, tetra- or pentasubstituted by fluorine, chlorine or        mono- or disubstituted by cyano, and of phenyl, benzyl, pyridyl,        pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl,        pyridinylmethyl and thiazolylmethyl, each of which is optionally        mono- to trisubstituted by C₁-C₄-alkyl, C₁-C₃-haloalkyl,        C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, cyclopropyl, fluorine, chlorine,        bromine or cyano,

    -   R¹⁹ represents hydrogen, an alkali or alkaline earth metal ion,        represents an ammonium ion which is optionally mono- to        tetrasubstituted by C₁-C₄-alkyl or represents a radical from the        group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₂-alkyl and C₁-C₄-alkyl-S—C₁-C₂-alkyl,        C₁-C₄-alkyl-S(O)—C₁-C₂-alkyl and C₁-C₄-alkyl-S(O)₂—C₁-C₂-alkyl,        each of which is optionally mono-, di-, tri-, tetra- or        pentasubstituted by fluorine, chlorine or mono- or disubstituted        by cyano, or

    -   R²², if R² represents the radical c), represents a radical from        the group consisting of C₁-C₆-alkyl, optionally        cyano-substituted C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyloxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,        C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyloxy,        C₁-C₄-alkylsulfinyl-C₁-C₄-alkyloxy,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyloxy,        C₁-C₄-haloalkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfinyl-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfonyl-C₂-C₄-alkenyl,        C₂-C₄-alkenylthio-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfinyl-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₄-haloalky        lcarbonyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy carbonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylaminosulfonyl,        di-(C₁-C₄-alkyl)-aminosulfonyl,

    -   R²³, if R² represents the radical c), represents a radical from        the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₂-C₄-alkenylthio-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl,

    -   R²², if R² represents the radical d), represents a radical from        the group consisting of C₁-C₄-alkyl, optionally        cyano-substituted C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfinyl-C₁-C₄-alkyl,        C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfinyl-C₂-C₄-alkenyl,        C₁-C₄-alkylsulfonyl-C₂-C₄-alkenyl,        C₂-C₄-alkenylthio-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfinyl-C₁-C₄-alkyl,        C₂-C₄-alkenylsulfonyl-C₁-C₄-alkyl,        C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₄-haloalky        lcarbonyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₄-haloalkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylaminosulfonyl,        di-(C₁-C₄-alkyl)-aminosulfonyl,

    -   R²³, if R² represents the radical d) or e), represents a radical        from the group consisting of hydrogen, C₁-C₆-alkyl,        C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,        C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyloxy,        C₁-C₄-alkylthio-C₁-C₄-alkyl, C₂-C₄-alkenylthio-C₁-C₄-alkyl,        cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄alkyl, and        -   in the case R²=d),

    -   R²² also represents optionally halogen-, cyano-, nitro-, amino-,        hydroxy-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₂-C₆-alkenyl-,        C₂-C₆-alkynyl-, C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-, C₃-C₆-alkenyloxy-, C₃-C₆-alkynyloxy-,        C₁-C₆-alkoxycarbonyloxy-, C₁-C₆-alkylamino-,        C₃-C₆-alkenylamino-, C₃-C₆-alkynylamino-,        C₃-C₆-cycloalkylamino-, C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-,        C₃-C₆-alkenylthio-, C₃-C₆-alkynylthio-, C₃-C₆-cycloalkylthio-,        C₁-C₆-alkylsulfinyl-, C₁-C₆-alkylsulfonyl-,        C₁-C₆-alkylcarbonyl-, aminocarbonyl-, C₁-C₆-alkylaminocarbonyl-,        di-(C₁-C₆-alkyl)-aminocarbonyl-,        C₁-C₆-alkylcarbonylamino-substituted phenyl or represents one of        the E radicals below

-   -   R²⁷ represents hydrogen or methyl and    -   R²⁶ represents a radical from the group consisting of hydrogen,        methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl,        propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl,        methylthioethyl, methylsulfinylethyl, methylsulfonylethyl and        cyanomethyl.

Range of preference (4): A particular group of compounds of the formula(I) is that of those in which

-   -   A represents a radical from the group consisting of (A-a), (A-b)        and (A-f)

-   -   -   where the broken line represents the bond to the nitrogen            atom of the bicyclic system of the formula (I),

    -   G¹ represents N or C—B¹,

    -   B¹ represents a radical from the group consisting of hydrogen        and fluorine,

    -   B² represents hydrogen,

    -   T represents an electron pair,

    -   R² c) represents the radical of the formula

-   -   -   where the broken line denotes the bond to the carbon atom of            the bicyclic system of the formula (I),

    -   X represents oxygen,

    -   R³ represents C₁-C₄-alkyl,

    -   R²² represents a radical from the group consisting of        C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₄-alkylsulfonyl and di-(C₁-C₄-alkyl)-aminosulfonyl and

    -   R²³ represents hydrogen or C₁-C₆-alkyl.

When sulfur and/or nitrogen occur in rings in the above definitions, forexample in expressions such as “in which the rings may contain at leastone heteroatom from the group of sulfur, oxygen (where oxygen and sulfuratoms must not be directly adjacent to one another) and nitrogen” or “inwhich one or two ring members may each be replaced by a heteroatom fromthe group of sulfur, oxygen (where oxygen atoms must not be directlyadjacent to one another) and nitrogen”, unless stated otherwise, thesulfur may also be present in the form of SO or SO₂; the nitrogen, if itis not in the form of —N═, as well as NH, may also be present in theform of N-alkyl (in particular N—C₁-C₆-alkyl).

In the preferred definitions whose combination forms the range ofpreference (1), unless stated otherwise,

cation represents an alkali metal ion selected from the group consistingof lithium, sodium, potassium, rubidium, caesium, preferably from thegroup consisting of lithium, sodium, potassium, or an

alkaline earth metal ion selected from the group consisting ofberyllium, magnesium, calcium, strontium, barium, preferably from thegroup consisting of magnesium and calcium,

halogen is selected from the group consisting of fluorine, chlorine,bromine and iodine, preferably in turn from the group consisting offluorine, chlorine and bromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group consisting of phenyl, naphthyl, anthryl,phenanthrenyl, and preferably in turn represents phenyl,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group consisting offuryl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzoisofuryl, benzothienyl,benzoisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl,benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl,2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl,

heterocyclyl represents a saturated 4-, 5- or 6-membered ring containing1 or 2 nitrogen atoms and/or one oxygen atom and/or one sulfur atom, forexample azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl,dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl, piperazinyl,morpholinyl.

In the particularly preferred definitions whose combination forms therange of preference (2), unless stated otherwise,

cation represents an alkali metal ion selected from the group consistingof lithium, sodium, potassium, rubidium, caesium, preferably from thegroup consisting of lithium, sodium, potassium, or an

alkaline earth metal ion selected from the group consisting ofberyllium, magnesium, calcium, strontium, barium, preferably from thegroup consisting of magnesium and calcium,

halogen is selected from the group consisting of fluorine, chlorine,bromine and iodine, preferably in turn from the group consisting offluorine, chlorine and bromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group consisting of phenyl, naphthyl, anthryl,phenanthrenyl, and preferably in turn represents phenyl,

hetaryl (synonymous with heteroaryl, also as part of a larger unit suchas, for example, hetarylalkyl) is selected from the group consisting ofpyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl,pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,

heterocyclyl is selected from the group consisting of azetidinyl,azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl,thiolanyl, thianyl, tetrahydrofuryl, piperazinyl, morpholinyl.

In the very particularly preferred definitions and the especiallypreferred definitions whose combination forms the range of preference(3), unless stated otherwise,

cation represents an alkali metal ion from the group consisting oflithium, sodium, potassium, rubidium, caesium, preferably from the groupconsisting of lithium, sodium, potassium, or an

alkaline earth metal ion from the group consisting of beryllium,magnesium, calcium, strontium, barium, preferably from the groupconsisting of magnesium and calcium,

heterocyclyl represents oxetanyl, thiethanyl, tetrahydrofuryl andmorpholinyl.

Aryl represents phenyl,

hetaryl (synonymous with heteroaryl, including as part of a larger unitsuch as, for example, hetarylalkyl) represents a radical from the groupconsisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl andpyrazolyl.

In the definitions which form the range of preference (4),

halogen represents fluorine, chlorine, bromine and iodine, preferably inturn fluorine, chlorine and bromine.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. In this case, halogen represents fluorine, chlorine, bromineor iodine, in particular fluorine, chlorine or bromine.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,may each be straight-chain or branched if possible, including incombination with heteroatoms, as, for example, in alkoxy.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutions may be the same or different.

If T in the radical A of the formula (A-a)

represents an electron pair, the radical is present as a pyridinederivative of the formula

If T in the radical A of the formula (A-a)

represents oxygen, the radical is present as a pyridine N-oxidederivative of the formula

Here, the formal charges (+ at nitrogen and − at oxygen) were omittedfrom the illustration.

The radical definitions or elucidations given in general terms or listedwithin areas of preference apply correspondingly to end products and tostarting materials and intermediates. These radical definitions can becombined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

According to the invention, preference is given to compounds of theformula (I) which contain a combination of the definitions listed aboveas being preferred (range of preference (1)).

According to the invention, particular preference is given to compoundsof the formula (I) which contain a combination of the definitions listedabove as being particularly preferred (range of preference (2)).

According to the invention, very particular preference is given tocompounds of the formula (I) which contain a combination of thedefinitions listed above as being very particularly preferred (range ofpreference (3)).

According to the invention, special preference is given to compounds ofthe formula (I) which contain a combination of the definitions listedabove as being special (range of preference (4)).

A preferred embodiment of the invention relates to compounds of theformula (I) in which A represents the radical of the formula (A-a)

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which A represents the radical of the formula (A-b)

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which A represents the radical of the formula (A-f)

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which A represents pyridin-3-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which A represents 5-fluoropyridin-3-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which A represents pyrimidin-5-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which A represents pyridazin-4-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² has the meanings given under a).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² has the meanings given under b).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² has the meanings given under c).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² has the meanings given under d).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² has the meanings given under e).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² has the meanings given under f).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R² represents the radical (D-2)

The radical definitions or elucidations given above in general terms orwithin preferred ranges apply correspondingly to the end products(including the compounds of the formulae (I-A) to (I-N) shown later),and to the starting materials and intermediates. These radicaldefinitions can be combined with one another as desired, i.e. includingcombinations between the respective ranges of preference.

In a preferred embodiment, the invention relates to compounds of theformula (I-A)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-B)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-C)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-D)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-E)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-F)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-G)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-H)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-I)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-J)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-K)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-L)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-M)

In a further preferred embodiment, the invention relates to compounds ofthe formula (I-N)

In the formulae (I-A) to (I-N), the variables G², R, R³, R⁸, R²², R²³ W,X¹, Y² and n have the meanings mentioned above.

The compounds of the formula (I) according to the invention and theiracid addition salts and metal salt complexes are highly active, inparticular in the control of animal pests including arthropods and inparticular insects.

The compounds of the formula (I) may possibly also, depending on thenature of the substituents, be in the form of stereoisomers, i.e. in theform of geometric and/or optical isomers or isomer mixtures of varyingcomposition. This invention provides both the pure stereoisomers and anydesired mixtures of these isomers, even though it is generally onlycompounds of the formula (I) that are discussed here.

The invention therefore relates both to the pure enantiomers anddiastereomers and to mixtures thereof for controlling animal pests,including arthropods and particularly insects.

However, preference is given in accordance with the invention to usingthe optically active, stereoisomeric forms of the compounds of theformula (I) and salts thereof.

Suitable salts of the compounds of the general formula (I) includecustomary nontoxic salts, i.e. salts with appropriate bases and saltswith added acids. Preference is given to salts with inorganic bases,such as alkali metal salts, for example sodium, potassium or caesiumsalts, alkaline earth metal salts, for example calcium or magnesiumsalts, ammonium salts, salts with organic bases and with inorganicamines, for example triethylammonium, dicyclohexylammonium,N,N′-dibenzylethylenediammonium, pyridinium, picolinium orethanolammonium salts, salts with inorganic acids, for examplehydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, orphosphates, salts with organic carboxylic acids or organic sulfonicacids, for example formates, acetates, trifluoroacetates, maleates,tartrates, methanesulfonates, benzenesulfonates orpara-toluenesulfonates, salts with basic amino acids, for examplearginates, aspartates or glutamates, and the like.

It has additionally been found that the compounds of the formula (I) canbe prepared by the processes described below.

Compounds of the formula (I) in which the heterocycle A representsoptionally B²-substituted pyrimidin-5-yl (A-a; G¹=N), pyridin-3-yl (A-a;G¹=C—B¹), pyrazin-2-yl (A-b), pyridazin-3-yl (A-c), thiazol-5-yl (A-d),isothiazol-4-yl (A-e) and pyrazol-4-yl (A-f) can, for example, beprepared according to Reaction Scheme I in two steps.

In Reaction Scheme I, A and R², unless indicated otherwise, have themeanings mentioned above.

For example, the 2-substituted 5-nitro-4-pyridinecarboxaldehydes of theformula (A-1) can be reacted with the corresponding 3-amino-substitutedheterocycles of the formula (A-2) in the presence of acidic reactionauxiliaries in a first reaction step to give compounds of the formula(A-3) which are then, in a second reaction step, subjected to reductivecyclization in the presence of a suitable phosphorus(III) reagent, forexample triethyl phosphite, with formation of the compounds (A-4).

If, in the process according to the invention for preparing thecompounds of the formula (I), the compound of the formula (A-1) employedis methyl 4-formyl-5-nitro-2-pyridinecarboxylate (R²═COOCH₃) and thecompound of the formula (A-2) employed is 3-pyridineamine(A=pyridin-3-yl), initially the methyl4-[(1E)-2-(dimethylamino)ethenyl]-5-nitro-2-pyridinecarboxylate(A=3-pyridin-3-yl, R²═COOCH₃) is formed as so-called “Schiff base”.Subsequent reduction and cyclization then leads to the 5-substituted2-(pyridin-3-yl)-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (A-4,A=pyridin-3-yl, R²═COOCH₃), which can be used as starting material forthe compounds of the formula (I) (cf. preparation examples).

Azomethine derivatives or so-called “Schiff bases” of amino-substitutesheterocycles have various applications (they form, for example, metalcomplexes or are biologically active) and can be obtained by customaryprocesses (cf. also V. Shama, et al., Intern. J. Univ. Pharm. BioScience 2013, 2, 241-57 and the literature cited therein).

Some of the compounds of the formula (A-1) are known and commerciallyavailable (e.g. for R²═Br, 2-bromo-5-nitroisonicotinaldehyde/AnichemProduct List), or they can be obtained by preparation processes known inprinciple (for R²═Cl; 2-chloro-5-nitro-4-pyridinecarboxaldehyde, WO2010/026121 A1; R²═NH₂; 2-amino-5-nitro-4-pyridinecarboxaldehyde, M.Andaloussi et al., Tetrahedron Lett. 48, 8392-8395, 2007).

For example, methyl 4-formyl-5-nitro-2-pyridinecarboxylate (R²═COOCH₃)can be synthesized from methyl 4-methyl-5-nitro-2-pyridinecarboxylatevia N,N-dimethylformamide O,O-dimethyl acetal reaction and subsequentsodium periodate oxidation according to Reaction Scheme II (cf.preparation examples, synthesis of intermediates).

Some of the compounds of the formula (A-2) are known and commerciallyavailable and/or they can be prepared by preparation processes known inprinciple, cf., for example, for A=5-fluoropyridin-3-yl (A-a; B²═H,G¹=C—F; T=electron pair) (WO 2011/123751 A2); pyrazin-2-yl (A-b; B²═H)(WO 2012/151567 A1); pyridazin-4-yl (A-c; B²═H) (WO 2011/038572 A1);thiazol-5-yl (A-d; B²═H) (JP 4600 6049 B4); isothiazol-4-yl (A-e; B²═H)(U.S. Pat. No. 2,839,529) or 1-methyl-1H-pyrazol-4-yl (A-f; B²═H,R³═CH₃).

The compounds of the formula (A-3) can be obtained by step 1 of thepreparation process mentioned, or by synthesis methods known inprinciple, cf., for example, the preparation of4-methyl-N-[(3-nitro-4-pyridinyl)methylene]benzamine (H. E. Baumgartenet al., J. Amer. Chem. Soc. 77, 2438-2440, 1955).

Finally, the compounds of the formula (I) can be obtained by Step 2 ofthe preparation process mentioned by reductive cyclization of the4-imino-5-nitropyridines of the formula (A-3), for example by theCandogan indazole synthesis in the presence of triethyl phosphite (cf.J. I. G. Candogan et al., J. Chem. Soc. 1965, 4831; N. E. Genung et al.,Org. Lett. 16, 3114-3117, 2014 and synthesis of azaindoles: WO2008/147822 A1 and WO 2010/056999).

Alternatively, it is also possible to utilize modified Candogan et al.reductive cyclization reaction conditions or to employ alternativereaction conditions, for example the transition metal-catalyzedreductive cyclization of iminonitroaromatics and the thermal transitionmetal-catalyzed cyclization of 2-azidoimines (cf. N. E. Genung et al.,Org. Lett. 2014, 16, 3114-3117 and the literature cited therein).

In the presence of the phosphorus(III) reagent, initially the nitrogroup in substrate (A-3) is reduced with formation of a nitroso group(cf. N. E. Genung et al., Org. Lett. 2014, 16, 3114-3117) whichsubsequently forms a nitrene or a nitrene-like intermediate which thencauses intramolecular cyclization. Besides triethyl phosphite, it isalso possible to use tricyclohexylphosphine, tri(n-butyl)phosphine ortri(tert-butyl)phosphine (M.-A. Armour et al., J. Chem. Soc., PerkinTrans. 2 1975, 1185-1189; N. E. Genung et al., Org. Lett. 2014, 16,3114-3117) as alternative phosphorus(III) reagents.

Compounds of the formula (I) in which R² represents a radical from thegroup consisting of (B-1) to (B-36) can be prepared, for example, fromcompounds of the formula (I) in which R² represents halogen from thegroup consisting of bromine and iodine, by known methods (Method A: cf.J. C. Antilla et al., J. Org. Chem., 2004, 69, 5578-5587 and Method B:cf. H. Dong et al., Org. Lett., 2011, 13, 2726-2729; Ch. O. Ndubaku etal., J. Med. Chem., 2013, 56, 4597-4610; T. Furuya et al., J. Am. Chem.Soc., 2010, 132, 3793-3807).

Compounds of the formula (I) in which R² represents halogen, for examplebromine or iodine, can be obtained according to Reaction Scheme I fromthe corresponding 2-halogenated 6-formyl-5-nitropyridines (A-1).

For example, the compounds of the formula (I) in which R² represents aradical (B-2), (B-21) or (B-23) can be obtained according to ReactionScheme III.

In Reaction Scheme III, the compounds (I-e) and (B-21) in which G² hasthe meaning mentioned further above have a nucleofugic leaving group LG,which is optionally generated in situ.

Compounds of the formula (I) in which R² represents a radical (B-1),(B-2), (B-10), (B-29) or (B-30) can be prepared by Method A, which isknown from the literature, preferably in the presence of copper(I)iodide and basic reaction auxiliaries, for exampletrans-N,N′-dimethylcyclohexane-1,2-diamine and potassium carbonate, in asuitable solvent or diluent. Useful solvents or diluents include allinert organic solvents, for example aliphatic or aromatic hydrocarbons.

Preference is given to using aromatic hydrocarbons such as, for example,toluene.

The preparation of the compounds of the formula (I) in which R²represents a radical (B-3) to (B-9), (B-11) to (B-28) and (B-31) to(B-33) can take place similar to Methods B and C shown in ReactionScheme III.

For example, the compounds (B-3) to (B-9), (B-11) to (B-28) and (B-31)to (B-33) having a suitable leaving group (LG=B(OH)₂) or(hetero)arylboronic ester (LG=B(OR)₂) can be reacted with theappropriate compounds of the formula (I-a) according to known methods(cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695;Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F.Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004) in the presence ofsuitable catalysts from the group of the transition metal salts to givecompounds of the formula (I-B-3) to (I-B-9), (I-B-11) to (I-B-28) and(I-B-31) to (I-B-33).

Some of the compounds (B-3) to (B-9), (B-11) to (B-13) and (B-21) to(B-33) having a suitable leaving group (LG=B(OH)₂ or (hetero)arylboronicester, LG=B(OR)₂) are known or they can be prepared by generally knownmethods: e.g. 1-(methyl-1H-pyrazol-4-yl)boronic acid [(B-3), LG=B(OH)₂,G²=hydrogen, WO 2009/155527],2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxazole [(B-6),LG=B(OCMe₂)₂, G²=phenyl, WO 2010/094755]; thiazol-2-ylboronic acid[(B-7), LG=B(OH)₂, G²=hydrogen, U.S. Pat. No. 6,310,095 B1];5-phenyl-1,2,4-thiadiazol-3-ylboronic acid [(B-13), LG=B(OH)₂,G²=phenyl, DE 19710614 A1], pyridin-3-ylboronic acid [(B-21) vs (B-22),LG=B(OH)₂, G²=hydrogen, WO 2013/186089]; 1,3,5-triazin-2-ylboronic acid[(B-28), LG=B(OH)₂, G²=hydrogen, KR 2011/079401].

Alternatively, the compounds of the formula (I-a) can initially beconverted by methods known from the literature into compounds of theformula (I-e) which are then reacted further with halogen-activatedheterocycles according to Reaction Scheme III by Method C (cf. T.Ishiyama et al., J. Org. Chem., 1995, 60, 7508-7510; WO 2010/151601).

Some halogen-activated compounds (B-3) to (B-9), (B-11) to (B-13) and(B-21) to (B-33) are known or can be prepared by generally knownmethods: e.g. 3-bromo-4,5-dihydro-1-phenyl-1H-pyrazole [(B-18), LG=Br,G²=phenyl, J. Elguero et al., Bull. Soc. Chim. France 1996, 5,1683-1686].

The preparation of compounds of the formula (I) in which R² represents aradical (B-21) or (B-23) can be carried out similar to Methods B and C,which are known from the literature and shown in Reaction Scheme III,preferably in the presence of suitable coupling catalysts, basicreaction auxiliaries and in a suitable solvent or diluent. Usefulsolvents or diluents include all inert organic solvents, for examplealiphatic or aromatic hydrocarbons.

Preference is given to using aromatic hydrocarbons such as, for example,toluene.

The preparation of compounds of the formula (I) in which R² represents aradical (B-3) to (B-9), (B-11) to (B-28) and (B-31) to (B-33) can becarried out similar to Methods B and C, which are shown in ReactionScheme III, preferably in the presence of suitable coupling catalysts,basic reaction auxiliaries and in a suitable solvent or diluent.

Examples of preferred coupling catalysts include palladium catalystssuch as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) ortetrakis(triphenylphosphine)palladium.

Suitable basic reaction auxiliaries used for carrying out the processesaccording to Reaction Scheme III are preferably carbonates of sodium orpotassium.

Preference is given to using nitriles such as acetonitrile,benzonitrile, in particular acetonitrile, or ethers such as diethylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular1,2-dimethoxyethane in combination with water.

Compounds of the formula (I) in which R² represents a radical from thegroup consisting of (C-1) to (C-9) or represents CX—NR²²R²³ can beprepared, for example, from compounds of the formula (I) in which R²represents a carboxyl group, following suitable activation (i.e. LGrepresents a nucleofugic leaving group optionally generated in situ) byknown methods.

For example, the compounds of the formula (I) in which R² represents aradical (C-1) or represents CX—NR²²R²³ can be obtained according toReaction Scheme IV (cf. also preparation examples for (I-C-1):A=5-fluoropyridin-3-yl; R⁸═H, R⁹═N(CH₃)₂, n=2 in Example 10; (I-d):A=pyridin-3-yl; R²², R²³═CH₃ in Example 7).

Compounds of the formula (I) in which R² represents carboxyl can beobtained according to Reaction Scheme I from corresponding methyl4-formyl-5-nitro-2-pyridinecarboxylates (A-1; R²═COOR). Subsequent esterhydrolysis by customary methods then leads to the compounds of theformula (I-b).

Suitable condensing agents for activating the carboxylic acids of theformula (I-b) are all condensing agents customarily used for suchamidation reactions. Examples include acid halide formers such asphosgene, phosgene derivatives such as carbonyldiimidazole (CDI),phosphorus trichloride, oxalyl chloride or thionyl chloride;carbodiimides such as N,N′-dicyclohexylcarbodiimide (DCC) and1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI), or other customarycondensing agents such as phosphorus pentoxide, polyphosphoric acid,N,N′-carbonyldiimidazole, 2-chloropyridine 1-methoiodide (Mukaiyama'sreagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/carbon tetrachloride, bromotripyrrolidinophosphoniumhexafluorophosphate (BROP),O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphoniumhexafluorophosphate (BOP), bis(2-oxo-3-oxazolidinyl)phosphinic chloride(BOP-Cl), N,N,N′,N′-bis(tetramethylene)chlorouronium tetrafluoroborate,O-(1H-benzotriazol-1yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate(HBTU), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uroniumhexafluorophosphate,O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate(TBTU), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uroniumtetrafluoroborate,O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt) and4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium salt (DMT.MM),usually available as chloride. These reagents can be used separately or,if appropriate, in combination.

However, for the targeted activation of the compounds of the formula(I-b) it is also possible to use mixed anhydrides (LG=COOR), which leadto the preparation of compounds of the formulae (I-C-1) and (I-d) (cf.G. W. Anderson et al. J. Am. Chem. Soc. 1967, 89, 5012-5017). Variouschloroformic esters can be employed in this process, such as, forexample, isobutyl chloroformate (LG=COOR where R=isobutyl) and isopropylchloroformate (LG=COOR where R=isopropyl). Likewise, it is possible forthis purpose to use diethylacetyl chloride, trimethylacetyl chloride andsimilar compounds.

The subsequent reaction of the activated compounds of the formula (I-c)with the respective amine components according to Reaction Scheme IV isoptionally carried out in the presence of a suitable reaction auxiliaryand in the presence of a suitable solvent or diluent.

Suitable reaction auxiliaries for carrying out the processes accordingto Reaction Scheme IV are basic reaction auxiliaries.

Examples which may be mentioned are the hydroxides, hydrides, oxides andcarbonates of lithium, sodium, potassium, magnesium, calcium and barium,furthermore further basic compounds such as amidine bases or guanidinebases, such as 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD);diazabicyclo[4.3.0]nonene (DBN), diazabicyclo[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undecene (DBU), cyclohexyltetrabutylguanidine(CyTBG), cyclohexyltetramethylguanidine (CyTMG),N,N,N,N-tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine,tertiary amines, such as triethylamine, trimethylamine, tribenzylamine,triisopropylamine, tributylamine, tricyclohexylamine, triamylamine,trihexylamine, N,N-dimethylaniline, N,N-dimethyltoluidine,N,N-dimethyl-p-aminopyridine, N-methylpyrrolidine, N-methylpiperidine,N-methylimidazole, N-methylpyrazole, N-methylmorpholine,N-methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine,4-dimethylaminopyridine, quinoline, α-picoline, β-picoline,isoquinoline, pyrimidine, acridine, N,N,N′,N′-tetramethylenediamine,N,N′,N′-tetraethylenediamine, quinoxaline, N-propyldiisopropylamine,N-ethyldiisopropylamine (“Hünig's Base”), N,N′-dimethylcyclohexylamine,2,6-lutidine, 2,4-lutidine or triethylenediamine

Suitable for use as basic reaction auxiliaries for carrying out theprocesses according to Reaction Scheme IV are all suitable acid binders,for example amines, in particular tertiary amines, and alkali metal andalkaline earth metal compounds.

For preparing the compounds of the formula (I-C-1) or (I-d), use ispreferably made of tertiary amines such as N-propyldiisopropylamine orN-ethyldiisopropylamine (DIEA; Hünig's base).

Suitable solvents or diluents include all inert organic solvents, forexample aliphatic or aromatic hydrocarbons (such as petroleum ether,toluene), halogenated hydrocarbons (such as chlorotoluene,dichloromethane, chloroform, 1,2-dichloroethane), ethers (such asdiethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane), esters(such as ethyl or methyl acetate), nitrohydrocarbons (such asnitromethane, nitroethane, nitrobenzene), nitriles (such asacetonitrile, benzonitrile), amides (such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone,hexamethylphosphoramide), and also dimethyl sulfoxide or water ormixtures of the solvents mentioned.

Preference is given to using amides as solvents, for exampleN,N-dimethylformamide.

Compounds of the formula (I) in which R² represents a radical from thegroup consisting of (D-1) to (D-3) can be prepared, for example, fromcompounds of the formula (I) in which R² represents halogen from thegroup consisting of bromine and iodine, by methods known in principle.

For example, the compounds of the formula (I) in which R² represents aradical from the group consisting of (D-1) to (D-3) can be obtainedaccording to Reaction Scheme V by methods known from the literature (cf.US2013/0267493; T. Furuya et al., J. Am. Chem. Soc., 2010, 132,3793-3807).

In Reaction Scheme V, the compounds (D-2) in which W represents S, SO orSO₂ have a nucleofugic leaving group LG, which is optionally generatedin situ.

For example, the compounds (D-1) to (D-3) having a suitable leavinggroup (LG=B(OH)₂) or (hetero)arylboronic ester (LG=B(OR)₂) can bereacted with the appropriate compounds of the formula (I-a) according toknown methods (cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58,9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. deMeijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004) in thepresence of suitable catalysts from the group of the transition metalsalts to give compounds of the formulae (I-D-1) to (I-D-3).

The preparation of compounds of the formula (I) in which R² represents aradical (D-1) to (D-3) can be carried out similar to Reaction Scheme V,preferably in the presence of suitable coupling catalysts, basicreaction auxiliaries and in a suitable solvent or diluent.

Examples of preferred coupling catalysts include palladium catalystssuch as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) ortetrakis(triphenylphosphine)palladium.

Suitable basic reaction auxiliaries used for carrying out the processesaccording to Reaction Scheme III are preferably carbonates of sodium orpotassium.

Preference is given to using nitriles such as acetonitrile,benzonitrile, in particular acetonitrile, or ethers such as diethylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular1,2-dimethoxyethane in combination with water.

Subsequent oxidation of the sulfur in the compounds of the formula(I-D-2) in which W represents sulfur leads to compounds of the formula(I-D-2) in which W represents SO or SO₂ (cf. Reaction Scheme V)

Compounds of the formula (I) in which W is SO (sulfoxides) or SO₂(sulfones) can be prepared from compounds of the formula (I) in which Wis S (thioethers) by oxidation by processes known from the literature,for example by means of an oxidizing agent in a suitable solvent ordiluent. Suitable oxidizing agents are, for example, diluted nitricacid, hydrogen peroxide, Oxone® and peroxycarboxylic acids, for examplemeta-chloroperbenzoic acid. Suitable solvents or diluents are inertorganic solvents, typically acetonitrile and halogenated solvents suchas dichloromethane, chloroform or dichloroethane, and water and alcoholssuch as methanol for the reaction with Oxone®.

A variety of methods are suitable for producing enantiomericallyenriched sulfoxides, as described by G. E. O'Mahony et al., in ARKIVOC(Gainesville, Fla., United States), 2011, 1, 1-110: metal-catalysedasymmetric oxidations of thioethers, for example with titanium orvanadium as the most frequently utilized catalyst sources, in the formof Ti(O^(i)Pr₄) or VO(acac)₂, together with a chiral ligand and anoxidizing agent such as tert-butyl hydroperoxide (TBHP),2-phenylpropan-2-yl hydroperoxide (CHP) or hydrogen peroxide;non-metal-catalysed asymmetric oxidations through use of chiraloxidizing agents or chiral catalysts; electrochemical or biologicalasymmetric oxidations and also kinetic resolution of sulfoxides andnucleophilic displacement (by Andersen's method).

Compounds of the formula (I) in which R² represents —NR²³—C(X)—R²² canbe obtained, for example, from compounds of the formula (I) in which R²represents —NHR²³ via N-acylation reaction using activated compounds ofthe formula LG-CX—R²² in which LG represents a nucleofugic leaving groupwhich is optionally generated in situ.

These compounds of the formula (I) in which R² represents —NHR²³ can beprepared from compounds of the formula (I) in which R² represents acarboxyl group according to Reaction Scheme VI, by known methods.

For example, compounds of the formula (I-f) can be obtained by Curtiusdegradation as described, for example, in Houben-Weyl, Methoden derOrganischen Chemie [Methods of Organic Chemistry], Volume XI/1 (GeorgThieme Verlag Stuttgart), p. 865.

Here, the compounds of the formula (I-b) can, for example, be reacteddirectly with diphenylphosphoryl azide (DPPA) in the presence oftert-butanol to give compounds of the formula (I-f).

From the compounds of the formula (I-f), it is possible to obtain thecompounds of the formula (I-g) by N-alkylation in a first reaction step,N-deblocking (i.e. cleavage of the Boc group) in a second reaction stepand subsequent N-acylation in a third reaction step.

The compounds of the formula (I-h) can be prepared by N-deblocking (i.e.cleavage of the Boc group) in a first reaction step and subsequentN-acylation in a second reaction step.

In general, for the removal of the protecting group, it is possible touse suitable acidic or basic reaction auxiliaries according to theliterature procedure. When protecting groups of the carbamate type areused, preference is given to using acidic reaction auxiliaries. When thetert-butyl carbamate protective group (Boc group) is used, for example,mixtures of mineral acids such as hydrochloric acid, hydrobromic acid,nitric acid, sulfuric acid, phosphoric acid or of organic acids such asbenzoic acid, formic acid, acetic acid, trifluoroacetic acid,methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid, in asuitable diluent such as water and/or an organic solvent such astetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate,ethanol or methanol are used. Preference is given to mixtures ofhydrochloric acid or acetic acid with water and/or an organic solventsuch as ethyl acetate.

Isomers

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention therefore encompassespure stereoisomers and any desired mixtures of these isomers.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection. Thispreferably excludes methods for surgical or therapeutic treatment of thehuman or animal body and diagnostic methods carried out on the human oranimal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection agents.

In the context of the present application, the term “pesticide” alsoalways encompasses the term “crop protection agent”.

The compounds of the formula (I), given good plant tolerance, favourablehomeotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, nematodes and molluscs, which are encountered inagriculture, in horticulture, in animal husbandry, in aquatic cultures,in forests, in gardens and leisure facilities, in the protection ofstored products and of materials, and in the hygiene sector. They canpreferably be used as pesticides. They are active against normallysensitive and resistant species and also against all or specific stagesof development. The abovementioned pests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coffeae, Oligonychusconiferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychusmangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychusyothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., forexample Panonychus citri (=Metatetranychus citri), Panonychus ulmi(=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychusmultidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalusspp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus,Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., forexample Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., forexample Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychusturkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp.,Vasates lycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., forexample Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agriotes spp., for example Agriotes linneatus, Agriotes mancus,Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum,Anoplophora spp., Anthonomus spp., for example Anthonomus grandis,Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., for exampleAtomaria linearis, Attagenus spp., Baris caerulescens, Bruchidiusobtectus, Bruchus spp., for example Bruchus pisorum, Bruchus rufimanus,Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., for exampleCeutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchusrapae, Chaetocnema spp., for example Chaetocnema confinis, Chaetocnemadenticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp.,Cosmopolites spp., for example Cosmopolites sordidus, Costelytrazealandica, Ctenicera spp., Curculio spp., for example Curculio caryae,Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestesferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp.,for example Diabrotica balteata, Diabrotica barberi, Diabroticaundecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata,Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocisspp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachnaspp., for example Epilachna borealis, Epilachna varivestis, Epitrixspp., for example Epitrix cucumeris, Epitrix fuscula, Epitrixhirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.,Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hyperapostica, Hypomeces squamosus, Hypothenemus spp., for exampleHypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae,Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp.,for example Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus(=Hyperodes) spp., Lixus spp., Luperomorpha xanthodera, Luperodes spp.,Lyctus spp., Megascelis spp., Melanotus spp., for example Melanotuslongulus oregonensis, Meligethes aeneus, Melolontha spp., for exampleMelolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., for example Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., z.B. Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., for example Phyllotretaarmoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotretastriolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus,Psylliodes spp., for example Psylliodes affinis, Psylliodeschrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis,Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus,Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., forexample Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae,Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechusspp., for example Sternechus paludatus, Symphyletes spp., Tanymecusspp., for example Tanymecus dilaticollis, Tanymecus indicus, Tanymecuspalliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp.,for example Tribolium audax, Tribolium castaneum, Tribolium confusum,Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., forexample Zabrus tenebrioides;

from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;

from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleiaheraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopotaspp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp.,Hypoderma spp., Liriomyza spp., for example Liriomyza brassicae,Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., for exampleLucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., for exampleMusca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit,Paratanytarsus spp., Paralauterborniella subcincta, Pegomya spp., forexample Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomusspp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., forexample Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta,Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex, Toxotrypana curvicauda;

from the order of the Hemiptera for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., for example Amrasca bigutulla, Amrasca devastans, Anuraphiscardui, Aonidiella spp., for example Aonidiella aurantii, Aonidiellacitrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., for exampleAphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphisglycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphismiddletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola,Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiellaspp., Aspidiotus spp., for example Aspidiotus nerii, Atanus spp.,Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis,Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp.,Brevicoryne brassicae, Cacopsylla spp., for example Cacopsylla pyricola,Calligypona marginata, Capulinia spp., Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea,Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus,Cicadulina mbila, Coccomytilus halli, Coccus spp., for example Coccushesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis,Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp.,Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspisspp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., forexample Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae,Dysmicoccus spp., Empoasca spp., for example Empoasca abrupta, Empoascafabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosomaspp., for example Eriosoma americanum, Eriosoma lanigerum, Eriosomapyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp.,Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica,Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsyllaspinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopteruspruni, Icerya spp., for example Icerya purchasi, Idiocerus spp.,Idioscopus spp., Laodelphax striatellus, Lecanium spp., for exampleLecanium corni (=Parthenolecanium corni), Lepidosaphes spp., for exampleLepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycormadelicatula, Macrosiphum spp., for example Macrosiphum euphorbiae,Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarvaspp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa,Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzusspp., for example Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzusornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri,Neomaskellia spp., Nephotettix spp., for example Nephotettix cincticeps,Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens,Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp.,Parabemisia myricae, Paratrioza spp., for example Paratrioza cockerelli,Parlatoria spp., Pemphigus spp., for example Pemphigus bursarius,Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccusspp., for example Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., for example Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., forexample Planococcus citri, Prosopidopsylla flava, Protopulvinariapyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., for examplePseudococcus calceolariae, Pseudococcus comstocki, Pseudococcuslongispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsisspp., Psylla spp., for example Psylla buxi, Psylla mali, Psylla pyri,Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp.,for example Quadraspidiotus juglansregiae, Quadraspidiotusostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcusspp., Rhopalosiphum spp., for example Rhopalosiphum maidis,Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphumrufiabdominale, Saissetia spp., for example Saissetia coffeae, Saissetiamiranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus,Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobionavenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephalafestina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephelaspp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., forexample Toxoptera aurantii, Toxoptera citricidus, Trialeurodesvaporariorum, Trioza spp., for example Trioza diospyri, Typhlocyba spp.,Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., for example Cimexadjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus,Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus,Diconocoris hewetti, Dysdercus spp., Euschistus spp., for exampleEuschistus heros, Euschistus servus, Euschistus tristigmus, Euschistusvariolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys,Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisavaricornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocorisspp., for example Lygocoris pabulinus, Lygus spp., for example Lyguselisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacoptacribraria, Miridae, Monalonion atratum, Nezara spp., for example Nezaraviridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata,Piezodorus spp., for example Piezodorus guildinii, Psallus spp.,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Camponotus spp.,Dolichovespula spp., Diprion spp., for example Diprion similis,Hoplocampa spp., for example Hoplocampa cookei, Hoplocampa testudinea,Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis,Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp.,Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp.,Vespa spp., for example Vespa crabro, Wasmannia auropunctata, Xerisspp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;

from the order of the Isoptera, for example Coptotermes spp., forexample Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermesspp., Odontotermes spp., Reticulitermes spp., for example Reticulitermesflavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra,Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseolaspp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsapomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., forexample Chilo plejadellus, Chilo suppressalis, Choreutis pariana,Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolophaaurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp.,for example Ephestia elutella, Ephestia kuehniella, Epinotia spp.,Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiellaspp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp.,for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleriamellonella, Gracillaria spp., Grapholitha spp., for example Grapholitamolesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., forexample Helicoverpa armigera, Helicoverpa zea, Heliothis spp., forexample Heliothis virescens, Hofmannophila pseudospretella, Homoeosomaspp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata,Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis,Leucoptera spp., for example Leucoptera coffeella, Lithocolletis spp.,for example Lithocolletis blancardella, Lithophane antennata, Lobesiaspp., for example Lobesia botrana, Loxagrotis albicosta, Lymantria spp.,for example Lymantria dispar, Lyonetia spp., for example Lyonetiaclerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae,Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata,Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp.,Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., for exampleOstrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp.,for example Pectinophora gossypiella, Perileucoptera spp., Phthorimaeaspp., for example Phthorimaea operculella, Phyllocnistis citrella,Phyllonorycter spp., for example Phyllonorycter blancardella,Phyllonorycter crataegella, Pieris spp., for example Pieris rapae,Platynota stultana, Plodia interpunctella, Plusia spp., Plutellaxylostella (=Plutella maculipennis), Prays spp., Prodenia spp.,Protoparce spp., Pseudaletia spp., for example Pseudaletia unipuncta,Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobiusspp., for example Schoenobius bipunctifer, Scirpophaga spp., for exampleScirpophaga innotata, Scotia segetum, Sesamia spp., for example Sesamiainferens, Sparganothis spp., Spodoptera spp., for example Spodopteraeradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica,Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedonspp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tineacloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp.,Trichophaga tapetzella, Trichoplusia spp., for example Trichoplusia ni,Tryporyza incertulas, Tuta absoluta, Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., for example Frankliniellafusca, Frankliniella occidentalis, Frankliniella schultzei,Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi,Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothripsspp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothripscardamomi, Thrips spp., for example Thrips palmi, Thrips tabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata;

pests from the phylum of the Mollusca, in particular from the class ofthe Bivalvia, for example Dreissena spp.;

and also from the class of the Gastropoda, for example Anion spp., forexample Anion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;

animal and human parasites from the phyla of the Platyhelminthes andNematoda, for example Aelurostrongylus spp., Amidostomum spp.,Ancylostoma spp, for example Ancylostoma duodenale, Ancylostomaceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakisspp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascarisspp., Brugia spp., for example Brugia malayi, Brugia timori, Bunostomumspp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp.,for example Dictyocaulus filaria, Diphyllobothrium spp., for exampleDiphyllobothrium latum, Dipylidium spp., Dirofilaria spp., Dracunculusspp., for example Dracunculus medinensis, Echinococcus spp., for exampleEchinococcus granulosus, Echinococcus multilocularis, Echinostoma spp.,Enterobius spp., for example Enterobius vermicularis, Eucoleus spp.,Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp.,Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp.,Heligmosomoides spp., Heterakis spp., Hymenolepis spp., for exampleHymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., forexample Loa Loa, Metastrongylus spp., Metorchis spp., Mesocestoidesspp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp.,Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocercaspp, for example Onchocerca volvulus, Opisthorchis spp., Oslerus spp.,Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp.,Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascarisspp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setariaspp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp.,Strongyloides spp., for example Strongyloides fuelleborni, Strongyloidesstercoralis, Strongylus spp., Syngamus spp., Taenia spp., for exampleTaenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Trichinella spp., for exampleTrichinella spiralis, Trichinella nativa, Trichinella britovi,Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp.,Trichostrongylus spp., Trichuris spp., for example Trichuris trichuria,Uncinaria spp., Wuchereria spp., for example Wuchereria bancrofti;

plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, especially Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., for example Longidorus africanus,Meloidogyne spp., for example Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., for example Paratrichodorus minor, Paratylenchusspp., Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

In addition, it is possible to control, from the sub-kingdom of theProtozoa, the order of the Coccidia, for example Eimeria spp.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). They can, as the case may be, also be used as intermediatesor precursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I).Optionally, the use forms comprise further pesticides and/or adjuvantswhich improve action, such as penetrants, e.g. vegetable oils, forexample rapeseed oil, sunflower oil, mineral oils, for example paraffinoils, alkyl esters of vegetable fatty acids, for example rapeseed oilmethyl ester or soya oil methyl ester, or alkanol alkoxylates and/orspreaders, for example alkylsiloxanes and/or salts, for example organicor inorganic ammonium or phosphonium salts, for example ammonium sulfateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulfosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active compounds.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries such as, for example,extenders, solvents and/or solid carriers and/or other auxiliaries suchas, for example, surfactants. The formulations are produced either insuitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulfones andsulfoxides (such as dimethyl sulfoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulfoxide, and water.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, suchas chlorobenzene, chloroethylene or methylene chloride, aliphatichydrocarbons, such as cyclohexane, paraffins, mineral oil fractions,mineral and vegetable oils, alcohols, such as methanol, ethanol,isopropanol, butanol or glycol and their ethers and esters, ketones suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethyl sulfoxide, andalso water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and natural or syntheticsilicates, resins, waxes and/or solid fertilizers. It is likewisepossible to use mixtures of such carriers. Useful carriers for granulesinclude: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite, dolomite, and synthetic granules ofinorganic and organic flours, and also granules of organic material suchas sawdust, paper, coconut shells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable are those extenders or carriers which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonicacid, polycondensates of ethylene oxide with fatty alcohols or withfatty acids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulfosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the compounds containing sulfates, sulfonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulfonates,alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite wasteliquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and if the application takesplace in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom are dyes such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients andtrace nutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam generatorsor antifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) can be combinedwith any solid or liquid additive commonly used for formulationpurposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulfosuccinate, or increaseviscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of agrochemically activecompounds into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and henceincrease the mobility of the active compounds in the cuticle. The methoddescribed in the literature (Baur et al., 1997, Pesticide Science 51,131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulfate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), more preferably between 0.01%and 95% by weight of the compound of the formula (I), most preferablybetween 0.5% and 90% by weight of the compound of the formula (I), basedon the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active compound combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used in mixtures with agents to improve plant properties, forexample growth, yield and quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case.

Insecticides/Acaricides/Nematicides

The active compounds specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos,chloropyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon,dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton,EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,fosthiazate, heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel antagonists, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators/voltage-gated sodium channel blockers, forexample pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin,d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin,empenthrin [(EZ)-(1R) isomers], esfenvalerate, etofenprox,fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin,phenothrin [(1R)-trans isomer], prallethrin, pyrethrins (pyrethrum),resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers)], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for exampleneonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.

(5) Allosteric activators of the nicotinergic acetylcholine receptor(nAChR), for example spinosyns, e.g. spinetoram and spinosad.

(6) Chloride channel activators, for example avermectins/milbemycins,e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone imitators, for example, juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Active compounds having unknown or nonspecific mechanisms of action,for example alkyl halides, e.g. methyl bromide and other alkyl halides;or chloropicrine or sulfuryl fluoride or borax or tartar emetic.

(9) Selective antifeedants, e.g. pymetrozine or flonicamid.

(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect gut membrane, e.g. Bacillusthuringiensis subspecies israelensis, Bacillus sphaericus, Bacillusthuringiensis subspecies aizawai, Bacillus thuringiensis subspecieskurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plantproteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,Cry34/35Ab1.

(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatin andfenbutatin oxide or propargite or tetradifon.

(13) Oxidative phosphorylation decouplers that interrupt the H protongradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for examplebistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting inhibitors (especially for Diptera, i.e. dipterans), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists, for example amitraz.

(20) Complex-III electron transport inhibitors, for examplehydramethylnon or acequinocyl or fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example METIacaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Complex-IV electron transport inhibitors, for example phosphines,e.g. aluminium phosphide, calcium phosphide, phosphine and zincphosphide or cyanide.

(25) Complex-II electron transport inhibitors, for example cyenopyrafenand cyflumetofen.

(28) Ryanodine receptor effectors, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide.

Further active ingredients having an unknown or unclear mechanism ofaction, for example afidopyropen, afoxolaner, azadirachtin, benclothiaz,benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,diflovidazin, flometoquin, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fufenozide, guadipyr,heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding,pyflubumide, pyridalyl, pyrifluquinazon, pyriminostrobin,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, triflumezopyrim and iodomethane; and additionallypreparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and thefollowing known active compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known fromWO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from CN102057925),8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide(known from WO2010/129500),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2009/080250),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,-3-trifluoroacetamide(known from WO2012/029672),1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN101337940),N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO2008/134969,3-[benzoyl(methyl)amino]-N-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluorobenzamide(known from WO 2010018714), butyl[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]carbonate(known from CN 102060818),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(Z)-methoxyiminomethyl]-2-methylbenzamide(known from WO2007/026965),3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213,N-(methylsulfonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboxamide(known from WO2012/000896),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926).

Fungicides

The active ingredients specified herein by their common name are knownand described, for example, in “Pesticide Manual” or on the Internet(for example: http://www.alanwood.net/pesticides).

All the fungicidal mixing components listed in classes (1) to (15) mayoptionally form salts with corresponding bases or acids if suitablefunctional groups are present. In addition, the fungicidal mixingcomponents listed in classes (1) to (15) also include tautomeric formsif tautomerism is possible.

1) inhibitors of the ergosterol biosynthesis, for example (1.01)aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole,(1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole,(1.08) diniconazole, (1.09) diniconazole-M, (1.10) dodemorph, (1.11)dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14)fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidin,(1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol,(1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24)furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalilsulfate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole,(1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34)oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole,(1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44)quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47)tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50)triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole,(1.54) triforin, (1.55) triticonazole, (1.56) uniconazole, (1.57)uniconazole-p, (1.58) viniconazole, (1.59) voriconazole, (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61)1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylicacid methyl ester, (1.62)N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,(1.64)O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate,(1.65) pyrisoxazole, (1.66)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.67)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate,(1.68)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.69)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.70)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.71)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.72) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate,(1.73)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocarbanate,(1.74)5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.75)5-(allylsulfanyl)-1-[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.76)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.77)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.78)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.79)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.80)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.81)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.82)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.83)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.84)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.85)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.86)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.87)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.88)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.89) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.90)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.91) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.92)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.93)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.94)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.95)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol.

2) Inhibitors of the respiratory chain on complex I or II, for example(2.01) bixafen, (2.02) boscalid, (2.03) carboxin, (2.04) diflumetorim,(2.05) fenfuram, (2.06) fluopyram, (2.07) flutolanil, (2.08)fluxapyroxad, (2.09) furametpyr, (2.10) furmecyclox, (2.11) isopyrazam(mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate1RS,4SR,9SR), (2.12) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR),(2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18)mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad,(2.22) sedaxane, (2.23) thifluzamide, (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine,(2.29) benzovindiflupyr, (2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.32)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.35)1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.36)1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.37)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.38)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.39)1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(2.43) isofetamid, (2.44)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.45)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.46)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.47)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.48)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.49)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.50)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.51) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (2.52)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.53)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.54)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.55)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.56) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (2.57)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(2.58)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(2.59)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.60)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(2.61)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.62)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.63)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(2.64)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.65)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.66)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.67)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide,(2.68)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.69)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.70)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain on complex III, for example(3.01) ametoctradin, (3.02) amisulbrom, (3.03) azoxystrobin, (3.04)cyazofamid, (3.05) coumethoxystrobin, (3.06) coumoxystrobin, (3.07)dimoxystrobin, (3.08) enoxastrobin, (3.09) famoxadon, (3.10) fenamidon,(3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl,(3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin,(3.17) pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin,(3.20) pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin,(3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,(3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)acetamide,(3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide,(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.27) fenaminostrobin, (3.28)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.29)(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylicacid methyl ester, (3.30)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.31)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.33)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide.

4) Inhibitors of mitosis and cell division, for example (4.01) benomyl,(4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05)ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron,(4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate,(4.12) zoxamide, (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,(4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

5) Compounds capable of having multisite action, for example (5.01)Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04) chlorothalonil,(5.05) copper hydroxide, (5.06) copper naphthenate, (5.07) copper oxide,(5.08) copper oxychloride, (5.09) copper(2+) sulfate, (5.10)dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13) dodine free base,(5.14) ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine,(5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadinealbesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23)mancozeb, (5.24) maneb, (5.25) metiram, (5.26) metiram zinc, (5.27)oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulfur andsulfur preparations including calcium polysulfide, (5.31) thiram, (5.32)tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine.

6) Compounds capable of inducing host defence, for example (6.01)acibenzolar-S-methyl, (6.02) isotianil, (6.03) probenazole, (6.04)tiadinil, (6.05) laminarin

7) Inhibitors of the amino acid and/or protein biosynthesis, for example(7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04)kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06)mepanipyrim, (7.07) pyrimethanil, (7.08)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(7.09) oxytetracycline, (7.10) streptomycin.

8) Inhibitors of ATP production, for example (8.01) fentin acetate,(8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.

9) Inhibitors of cell wall synthesis, for example (9.01)benthiavalicarb, (9.02) dimethomorph, (9.03) flumorph, (9.04)iprovalicarb, (9.05) mandipropamid, (9.06) polyoxins, (9.07) polyoxorim,(9.08) validamycin A, (9.09) valifenalate, (9.10) polyoxin B, (9.11)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.12)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Inhibitors of lipid and membrane synthesis, for example (10.01)biphenyl, (10.02) chloroneb, (10.03) dicloran, (10.04) edifenphos,(10.05) etridiazole, (10.06) iodocarb, (10.07) iprobenfos, (10.08)isoprothiolane, (10.09) propamocarb, (10.10) propamocarb hydrochloride,(10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14)tecnazene, (10.15) tolclofos-methyl.

11) Inhibitors of melanin biosynthesis, for example (11.01) carpropamid,(11.02) diclocymet, (11.03) fenoxanil, (11.04) phthalide, (11.05)pyroquilon, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Inhibitors of nucleic acid synthesis, for example (12.01) benalaxyl,(12.02) benalaxyl-M (kiralaxyl), (12.03) bupirimate, (12.04) clozylacon,(12.05) dimethirimol, (12.06) ethirimol, (12.07) furalaxyl, (12.08)hymexazole, (12.09) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11)ofurace, (12.12) oxadixyl, (12.13) oxolinic acid, (12.14) octhilinone.

13) Inhibitors of signal transduction, for example (13.01) chlozolinate,(13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05)procymidone, (13.06) quinoxyfen, (13.07) vinclozolin, (13.08)proquinazid.

14) Compounds capable of acting as uncouplers, for example (14.01)binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04) fluazinam,(14.05) meptyldinocap.

15) Further compounds, for example (15.001) benthiazole, (15.002)bethoxazin, (15.003) capsimycin, (15.004) carvone, (15.005)quinomethionate, (15.006) pyriofenone (chlazafenone), (15.007) cufraneb,(15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide,(15.011) dazomet, (15.012) debacarb, (15.013) dichlorophen, (15.014)diclomezin, (15.015) difenzoquat, (15.016) difenzoquat metilsulfate,(15.017) diphenylamine, (15.018) Ecomate, (15.019) fenpyrazamine,(15.020) flumetover, (15.021) fluoroimide, (15.022) flusulfamide,(15.023) flutianil, (15.024) fosetyl-aluminium, (15.025)fosetyl-calcium, (15.026) fosetyl-sodium, (15.027) hexachlorobenzene,(15.028) irumamycin, (15.029) methasulfocarb, (15.030) methylisothiocyanate, (15.031) metrafenone, (15.032) mildiomycin, (15.033)natamycin, (15.034) nickel dimethyldithiocarbamate, (15.035)nitrothal-isopropyl, (15.036) oxamocarb, (15.037) oxyfenthiin, (15.038)pentachlorophenol and salts, (15.039) phenothrin, (15.040) phosphorousacid and salts thereof, (15.041) propamocarb-fosetylate, (15.042)propanosin-sodium, (15.043) pyrimorph, (15.044) pyrrolnitrin, (15.045)tebufloquin, (15.046) tecloftalam, (15.047) tolnifanid, (15.048)triazoxide, (15.049) trichlamid, (15.050) zarilamid, (15.051)2-methylpropanoic acid(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-ylester, (15.052)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.053)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.054) oxathiapiproline, (15.055) 1H-imidazole-1-carboxylic acid1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl ester, (15.056)2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (15.057)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.058)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.059)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.060)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.061)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(15.062) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.063)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.064) 2-phenylphenol and salts, (15.065)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.066) 3,4,5-trichloropyridine-2,6-dicarboxylic acid nitrile, (15.067)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.068)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.069) 5-amino-1,3,4-thiadiazole-2-thiol, (15.070)5-chloro-N′-phenyl-N′-(prop-2-in-1-yl)thiophene-2-sulfonohydrazide,(15.071) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.072)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.073)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.074)(2Z)-3-amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.075)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.076)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-in-1-yloxy)phenyl]propanamide,(15.077)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-in-1-yloxy)phenyl]propanamide,(15.078)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(15.079)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(15.080)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(15.081)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.082)N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.083)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.084)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalin-1-yl)-1,3-thiazole-4-carboxamide,(15.085)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalin-1-yl]-1,3-thiazole-4-carboxamide,(15.086)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalin-1-yl]-1,3-thiazole-4-carboxamide,(15.087){6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamicacid pentyl ester, (15.088) phenazine-1-carboxylic acid, (15.089)quinolin-8-ol, (15.090) quinolin-8-ol sulfate (2:1), (15.091){6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamicacid tert-butyl ester, (15.092)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(15.093)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide,(15.094) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.095){6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamicacid but-3-yn-1-yl ester, (15.096) 4-amino-5-fluoropyrimidin-2-ol(tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.097)3,4,5-trihydroxybenzoic acid propyl ester, (15.098)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.099)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.100)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.101)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(15.102) 2-(6-benzylpyridin-2-yl)quinazoline, (15.103)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.104)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.105) abscisic acid, (15.106)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(15.107)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.108)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.109)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.110)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.111)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.112)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.113)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.114)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.115)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.116)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.117)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.118)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.119)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.120)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.121)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.122)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.123)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.124)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.125)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.126)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.127)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(15.128)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.129)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.130)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.131)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(15.132)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(15.133)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(15.134)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.135)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.136)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.137)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.138)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.139)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.140)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.141)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.142)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.143)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.144)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.145)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.146)N-(2-bromphenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.147)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.148)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.149)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.150)N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.151)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.152)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.153)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.154)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.155)N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.156)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.157)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.158)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.159)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.160)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.161)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.162)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.163)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate,(15.164)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate,(15.165)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.166)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.167)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.168)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.169)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.170)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.171)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate,(15.172)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate,(15.173)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate,(15.174)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides include especially bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM I-1562 or Bacillus firmus,strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii, (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (AccessionNumber CNCM I-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, bell peppers and chili peppers, cucumbers,melons, carrots, water melons, onions, lettuce, spinach, leeks, beans,Brassica oleracea (e.g. cabbage), peas and other vegetable species,cotton, tobacco, oilseed rape, and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes). Crop plants may be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant cultivars which are protectable or non-protectable by plantbreeders' rights. Plants shall be understood to mean all developmentalstages of the plants, for example seeds, cuttings and young (immature)plants up to mature plants. Plant parts shall be understood to mean allparts and organs of the plants above and below ground, such as shoot,leaf, flower and root, examples given being leaves, needles, stalks,stems, flowers, fruit bodies, fruits and seeds, and also roots, tubersand rhizomes. Plant parts also include harvested material (harvestedplants or plant parts) and vegetative and generative propagationmaterial, for example cuttings, tubers, rhizomes, slips and seeds.

The inventive treatment of the plants and parts of plants with thecompounds of the formula (I) is effected directly or by allowing them toact on the surroundings, habitat or storage space thereof by thecustomary treatment methods, for example by dipping, spraying,evaporating, fogging, scattering, painting on, injecting, and, in thecase of propagation material, especially in the case of seeds, also byapplying one or more coats.

As already mentioned above, it is possible to treat all plants and partsthereof in accordance with the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding methods, such as crossing or protoplastfusion, and parts thereof, are treated. In a further preferredembodiment, transgenic plants and plant cultivars obtained by geneticengineering methods, if appropriate in combination with conventionalmethods (genetically modified organisms), and parts thereof are treated.The term “parts” or “parts of plants” or “plant parts” has beenexplained above. Particular preference is given in accordance with theinvention to treating plants of the respective commercially customaryplant cultivars or those that are in use. Plant cultivars are understoodto mean plants having new properties (“traits”) and which have beengrown by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better capability for storage and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants against animal and microbial pests, such as insects, arachnids,nematodes, mites, slugs and snails, owing, for example, to toxins formedin the plants, in particular those formed in the plants by the geneticmaterial from Bacillus thuringiensis (for example by the genes CryIA(a),CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb andCryIF and also combinations thereof), and also increased resistance ofthe plants against phytopathogenic fungi, bacteria and/or virusescaused, for example, by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins, and also increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulfonylureas, glyphosates or phosphinothricin (forexample the “PAT” gene). The genes which impart the desired properties(“traits”) in question may also be present in combinations with oneanother in the transgenic plants. Examples of transgenic plants includethe important crop plants, such as cereals (wheat, rice, triticale,barley, rye, oats), maize, soya beans, potatoes, sugar beet, sugar cane,tomatoes, peas and other types of vegetable, cotton, tobacco, oilseedrape and also fruit plants (with the fruits apples, pears, citrus fruitsand grapes), particular emphasis being given to maize, soya beans,wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseed rape.Properties (“traits”) which are particularly emphasized are theincreased resistance of the plants to insects, arachnids, nematodes andslugs and snails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) directly or by action on their surroundings, habitat or storagespace using customary treatment methods, for example by dipping,spraying, atomizing, irrigating, evaporating, dusting, fogging,broadcasting, foaming, painting, spreading-on, injecting, watering(drenching), drip irrigating and, in the case of propagation material,in particular in the case of seed, additionally by dry seed treatment,liquid seed treatment, slurry treatment, by incrusting, by coating withone or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.compounds of the formula (I) are applied to the foliage, where treatmentfrequency and the application rate should be adjusted according to thelevel of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I) areintroduced in solid form (e.g. in the form of granules) into the locusof the plants. In the case of paddy rice crops, this can also beaccomplished by metering the compound of the formula (I) in a solidapplication form (for example as granules) into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed entails a series of problems whichcannot always be solved in a satisfactory manner. Thus, it is desirableto develop methods for protecting the seed and the germinating plantwhich dispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is additionally desirable to optimize theamount of active ingredient used so as to provide optimum protection forthe seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active ingredient used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and the germinating plant with a minimumexpenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It further alsocomprises a method where the seed is treated at different times with acompound of the formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) for protection from animal pests. Theinvention also relates to seed which has been treated simultaneouslywith a compound of the formula (I) and a mixing component. The inventionfurther relates to seed which has been treated at different times with acompound of the formula (I) and a mixing component. In the case of seedwhich has been treated at different times with a compound of the formula(I) and a mixing component, the individual substances may be present onthe seed in different layers. In this case, the layers comprising acompound of the formula (I) and a mixing component may optionally beseparated by an intermediate layer. The invention also relates to seedin which a compound of the formula (I) and a mixing component have beenapplied as part of a coating or as a further layer or further layers inaddition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages encountered with a systemically acting compound ofthe formula (I) is the fact that, by treating the seed, not only theseed itself but also the plants resulting therefrom are, afteremergence, protected against animal pests. In this way, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, this includes seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beet (for example sugar beet and fodder beet), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate in this case frommicroorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia,Trichoderma, Clavibacter, Glomus or Gliocladium. The present inventionis particularly suitable for the treatment of transgenic seed containingat least one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been pre-swollen in water up to a certainstage (pigeon breast stage) for example, which leads to improvedgermination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activeingredients which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing compoundsof the formula (I) with customary additives such as, for example,customary extenders and also solvents or diluents, dyes, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Alkyl naphthalenesulfonates, such asdiisopropyl or diisobutyl naphthalenesulfonates, can be used withpreference.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical ingredients. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants include in particularethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulfated derivatives thereof. Suitable anionic dispersants areespecially lignosulfonates, polyacrylic acid salts andarylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats and triticale, and also the seed of maize, rice, oilseed rape,peas, beans, cotton, sunflowers, soya beans and beets, or else a widevariety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or use forms prepared therefrom, allmixing units usable customarily for the seed dressing are useful.Specifically, the procedure in seed dressing is to place the seed into amixer in batchwise or continuous operation, to add the particulardesired amount of seed-dressing formulations, either as such or afterprior dilution with water, and to mix until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The application rate of the seed-dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasites”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects and acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable endotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer,and particularly cattle and pigs; poultry such as turkeys, ducks, geese,and particularly chickens; fish and crustaceans, for example inaquaculture, and also insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds, reptiles, amphibians and aquarium fish.

In a preferred embodiment, the compounds of the formula (I) areadministered to mammals.

In another preferred embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds and particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” means that the compounds of the formula (I) are effectivein reducing the incidence of the particular parasite in an animalinfected with such parasites to an innocuous degree. More specifically,“controlling” in the present context means that the compound of theformula (I) can kill the respective parasite, inhibit its growth, orinhibit its proliferation.

Arthropods include:

from the order Anoplurida, for example Haematopinus spp., Linognathusspp., Pediculus spp., Phtirus spp., Solenopotes spp.; from the orderMallophagida and the suborders Amblycerina and Ischnocerina, for exampleTrimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp.,Felicola spp.; from the order Diptera and the suborders Nematocerina andBrachycerina, for example Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitraspp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Luciliaspp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp.,Melophagus spp., Rhinoestrus spp., Tipula spp.; from the orderSiphonapterida, for example Pulex spp., Ctenocephalides spp., Tungaspp., Xenopsylla spp., Ceratophyllus spp.;

from the order Heteropterida, for example Cimex spp., Triatoma spp.,Rhodnius spp., Panstrongylus spp.; and also nuisance and hygiene pestsfrom the order Blattarida.

Arthropods further include:

from the subclass Acari (Acarina) and the order Metastigmata, forexample from the family Argasidae like Argas spp., Ornithodorus spp.,Otobius spp., from the family Ixodidae like Ixodes spp., Amblyomma spp.,Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp.,Hyalomma spp., Rhipicephalus spp. (the original genus of multi-hostticks); from the order Mesostigmata like Dermanyssus spp., Ornithonyssusspp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostomaspp., Varroa spp., Acarapis spp.; from the order Actinedida(Prostigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Neotrombiculla spp., Listrophorus spp.; and from theorder Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

Parasitic protozoa include:

Mastigophora (Flagellata), for example Trypanosomatidae, for exampleTrypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense,T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T.vivax, Leishmania brasiliensis, L. donovani, L. tropica, for exampleTrichomonadidae, for example Giardia lamblia, G. canis;

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for exampleEntamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp.,Harmanella sp.;

Apicomplexa (Sporozoa) such as Eimeridae, for example Eimeriaacervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E.arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E.chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E.debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E.flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina,E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, Eninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E.stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii,Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I.rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec.,in particular C. parvum; such as Toxoplasmadidae, for example Toxoplasmagondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; suchas Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S.ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such asLeucozoidae, for example Leucozytozoon simondi, such as Plasmodiidae,for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P. spec., such as Piroplasmea, for example Babesia argentina, B.bovis, B. canis, B. spec., Theileria parva, Theileria spec., such asAdeleina, for example Hepatozoon canis, H. spec.

Pathogenic endoparasites which are helminths include Platyhelmintha(e.g. Monogenea, cestodes and trematodes), nematodes, Acanthocephala,and Pentastoma. These include:

Monogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystomaspp.;

Cestodes: from the order of Pseudophyllidea, for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diphlogonoporus spp.;

from the order Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;

Trematodes: from the class of Digenea, for example: Diplostomum spp.,Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimusspp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimusspp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchisspp., Metorchis spp., Heterophyes spp., Metagonimus spp.;

Nematodes: Trichinellida, for example Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.,

from the order Tylenchida, for example: Micronema spp., Strongyloidesspp.;

from the order Rhabditida, for example: Strongylus spp., Triodontophorusspp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp.,Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp.,Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurusspp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp.,Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylusspp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp.,Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulusspp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp.,Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylusspp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp.,Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp.,Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirusspp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanusspp;

from the order Spirurida, for example: Oxyuris spp., Enterobius spp.,Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the orderPolymorphida for example: Filicollis spp.; from the order Moniliformidafor example: Moniliformis spp.;

from the order Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.;

Pentastoma: from the order Porocephalida, for example Linguatula spp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic ortherapeutic.

Thus, one embodiment of the present invention refers to the use of acompound of the formula (I) as a medicament.

A further aspect refers to the use of a compound of the formula (I) asan antiendoparasitic agent, in particular a helminthicidal agent orantiprotozoic agent. Compounds of the formula (I) are suitable for useas an antiendoparasitic agent, especially as a helminthicidal agent orantiprotozoic agent, for example in animal breeding, in animalhusbandry, in animal houses and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula(I) as an antiectoparasitic agent, in particular an arthropodicide suchas an insecticide or an acaricide. A further aspect relates to the useof a compound of the formula (I) as an antiectoparasitic agent, inparticular an arthropodicide such as an insecticide or an acaricide, forexample in animal husbandry, in animal breeding, in animal houses or inthe hygiene sector.

Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host or after injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of worms;    -   Aedes: yellow fever, dengue fever, filariasis, other viral        diseases;    -   Simuliidae: transmission of worms, in particular Onchocerca        volvulus;

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia duttoni, tick-borne encephalitis,Q fever (Coxiella burnetii), babesioses (Babesia canis canis).

Examples of vectors in the context of the present invention are insects,such as aphids, flies, leafhoppers or thrips, which can transmit plantviruses to plants. Other vectors capable of transmitting plant virusesare spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dims (malaria) and Culex, lice, fleas, flies, mites and ticks, which cantransmit pathogens to animals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in forests,in gardens and in leisure facilities, and also in the protection ofmaterials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. it can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic protection sector, in the hygiene protection sectorand in the protection of stored products, particularly for control ofinsects, arachnids and mites encountered in enclosed spaces, for exampledwellings, factory halls, offices, vehicle cabins. For controllinganimal pests, the compounds of the formula (I) are used alone or incombination with other active compounds and/or auxiliaries. They arepreferably used in domestic insecticide products. The compounds of theformula (I) are effective against sensitive and resistant species, andagainst all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is carried out, for example, in aerosols, unpressurizedspray products, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

Description of the Processes and Intermediates

The preparation and use examples which follow illustrate the inventionwithout limiting it. The products were characterized by ¹H NMRspectroscopy and/or LC-MS (Liquid Chromatography Mass Spectrometry).

The log P values were determined in accordance with OECD Guideline 117(EC Directive 92/69/EEC) by HPLC (high-performance liquidchromatography) using reversed-phase (RP) columns (C₁₈), by thefollowing methods:

[a] The LC-MS determination in the acidic range is carried out at pH 2.7with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formicacid) as eluents; linear gradient from 10% acetonitrile to 95%acetonitrile.

[b] LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.

Calibration is carried out using unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR spectra were determined using a Bruker Avance 400 fitted with aflow probe head (60 μl volume). In individual cases, the NMR spectrawere measured with a Bruker Avance II 600.

General synthesis of 5-substituted2-(hetaryl)-2H-pyrazolo[3,4-c]pyridines of the formula (I)

EXAMPLES 1 or 38

Step 1:

Synthesis of Compounds of the Formula (A-3) (R²═CO—OCH₃)

1 equivalent of a heterocyclic amino compound (A-2), 0.12 equivalent(3.4 mmol) of para-toluenesulfonic acid (PTSA) and 6 g of 4 A molecularsieve were added to a solution of 28.3 ml of 2-substituted5-nitro-4-pyridinecarboxaldehyde of the formula (A-1) in 200 ml oftoluene. The reaction mixture was then stirred at 110° C. for 16 hours.The reaction mixture was filtered and the filtrate gave, afterconcentration, the crude products (A-3), which were reacted furtherwithout further purification.

Step 2

Synthesis of 5-substituted 2-(hetaryl)-2H-pyrazolo[3,4-c]pyridines ofthe formula (I)

1 equivalent of the compounds of the formula (A-3) was dissolved in 30ml of triethyl phosphite, and the reaction mixture was then stirred at140° C. for about 16 hours. After concentration of the reaction mixtureunder reduced pressure, the residue that remained was purified by columnchromatography.

General synthesis of 5-substituted2-(hetaryl)-2H-pyrazolo[3,4-c]pyridine-5-carboxylic acids of the formula(I, R²═COOH)

1 equivalent of a compound of the formula (I; R²═COOCH₃) was dissolvedin a mixture of 100 ml of water and 100 ml of tetrahydrofuran, and 3equivalents of lithium hydroxide monohydrate were added. The reactionmixture was then stirred at 25° C. for about 16 hours. Subsequently, thetetrahydrofuran was removed under reduced pressure and the aqueous phasewas adjusted to pH=2 with 1M hydrochloric acid. After extraction with100 ml of ethyl acetate, the organic phase was dried over sodiumsulfate, filtered and concentrated under reduced pressure. The crudeproduct that remained was used in the next reaction step without furtherpurification.

a) 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniummethanaminiumhexafluorophosphate (HATU) coupling method

1.0 equivalent of 5-substituted2-(hetaryl)-2H-pyrazolo[3,4-c]pyridine-5-carboxylic acid was dissolvedin 3 ml of N,N-dimethylformaldehyde, and 2.4 equivalents (1.2 mmol) ofHATU and 6.0 equivalents of N,N-diisopropylethylamine were added. Thereaction mixture was then stirred at room temperature for 10 minutes,and 1.2 equivalents of the sulfonamide component were then added. Afterabout 16 hours of stirring at room temperature, the reaction mixture wasconcentrated under reduced pressure and the residue that remained waspurified by preparative chromatography (HPLC).

b) 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniummethanaminiumhexafluorophosphate (HATU) coupling method

1.0 equivalent of 5-substituted2-(hetaryl)-2H-pyrazolo[3,4-c]pyridine-5-carboxylic acid was dissolvedin 3 ml of N,N-dimethylformaldehyde, and 2.4 equivalents (1.2 mmol) ofHATU and 2.4 equivalents of N,N-diisopropylethylamine were added. Thereaction mixture was then stirred at room temperature for 10 minutes,and 1.2 equivalents of the amine component were then added. After about16 hours of stirring at room temperature, the reaction mixture wasconcentrated under reduced pressure and the residue that remained waspurified by preparative chromatography (HPLC).

Synthesis of Intermediates

Methyl 4-[(1E)-2-(dimethylamino)ethenyl]-5-nitro-2-pyridinecarboxylate

86.4 g (0.73 mmol) of N,N-dimethylformamide O,O-dimethyl acetal wereadded to a solution of 65 g (0.33 mol) of methyl5-methyl-6-nitro-3-pyridinecarboxylate (Y. Morisawa et al., J. Med.Chem. 21, 194-199, 1978) in 415 ml of N,N-dimethylformamide. Thereaction mixture was then stirred at 90° C. for 6 hours. The solvent wasthen removed under reduced pressure and the residue that remained waspurified by column chromatography. This gave 56 g (yield 66.7% oftheory) of methyl4-[(1E)-2-(dimethylamino)ethenyl]-5mitro-2-pyridinecarboxylate.

Methyl 4-formyl-5-nitro-2-pyridinecarboxylate

142 g (41.98 mmol) of sodium periodate were added to a solution of 56 g(0.22 mol) of methyl4-[(1E)-2-(dimethylamino)ethenyl]-5-nitro-2-pyridinecarboxylate in 550ml of water and 550 ml of tetrahydrofuran. The reaction mixture was thenstirred at 25° C. for 16 hours. The reaction mixture was then dilutedwith 700 ml of ethyl acetate and then washed with saturated aqueoussodium bicarbonate solution and brine. The combined organic phases weredried over sodium sulfate, filtered and concentrated under reducedpressure. The residue that remained was purified by columnchromatography. This gave 45 g (yield 97.3% of theory) of methyl4-formyl-5-nitro-2-pyridinecarboxylate as a brown solid.

TABLE 1 Compounds of the formula

Yield Purity Compound No. A R² [in mg] [in %] 1*)

 9.07  95.1 2 *)

 5.10 100 3 *)

 8.57  89.0 4 *)

 13.24  99.3 5 *)

 8.79  93.8 6 *)

 12.50 100 7 *)

 17.53  99.5 8 *)

 20.95  96.5 9 *)

 26.45  93.7 10 *)

 24.42  95.4 11

 42.50  92.2 12

 29.41  99.4 13

 29.98 100 14

 33.50  94.9 15 *)

 24.77  98.8 16

 24.33  98.1 17

 31.38  98.7 18 *)

 24.47  87.3 19

 36.67 100 20

 37.27  99.5 21*)

 22.16  98.5 22

 42.52  99.1 23 *)

 85.10 100 24 *)

 72.03 100 25

 93.41  90.8 26

 39.12  99.1 27

 46.42  97.1 28 *)

 42.0  99.3 29

 53.29  97.7 30 *)

 40.7  99.4 31

 43.30  99.1 32 *)

107.27  95.0 33 *)

 55.0  95.7 34 *)

 46.38 100 35 *)

 26.48  99.6 36

 33.96  99.2 37 *)

 21.32  98.2 38

 21.1  91.8 *) crystallizes with 1 x HCOOH

TABLE 2 Analytical data for the compounds 1-38 Reten- tion Ex. time No.[min] ¹H NMR [δ (ppm)] or LC-MS [m/z] 1 2.922 ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 1.65 (t, 3H, CH₃); 3.85 (m, 2H, CH₂); 8.57; 8.78; 8.90;8.96; 9.44; 9.58 (6H, ═CH, aryl/hetaryl). LC-MS = 319.1 (M + 1) [withoutHCOOH] 2 2.553 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 1.24 (d, 6H, 2xCH₃); 4.17(m, 1H, CH); 8.43; 8.51; 8.77; 8.88; 9.39; 9.56 (6H, ═CH, aryl/hetaryl).LC-MS = 283.2 (M + 1); [without HCOOH] 3 2.843 ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 3.78; 6.20 (2m, 3H, CH₂CHF₂); 8.51; 8.61; 8.80; 9.31;9.40; 9.57 (6H, ═CH, aryl/hetaryl); 9.05 (br., 1H, NH). LC-MS = 322.1(M + 1); [without HCOOH] 4 2.141 ¹H-NMR(400.0 MHz, d₆-DMSO): δ =1.15-1.26 (t + m, 5H, CH₂CH₃); 8.43; 9.37; 9.57; 9.60 (4H, ═CH,aryl/hetaryl); 8.80 (br., 1H, NH). LC-MS = 269.1 (M + 1) [without HCOOH]5 2.474 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.76; 6.20 (2m, 3H, CH₂CHF₂);8.48; 8.56; 8.77; 8.89; 9.42; 9.57 (6H, ═CH, aryl/hetaryl); 9.05 (br.,1H, NH). LC-MS = 305.1 (M + 1) [without HCOOH] 6 2.339 ¹H-NMR(400.0 MHz,CDCl₃): δ = 1.66 (t, 3H, CH₃); 3.84 (m, 2H, CH₂); 8.55; 9.37; 9.43; 9.60(4H, ═CH, aryl/hetaryl); 8.96 (br., 1H, NH). LC-MS = 319.0 (M + 1)[without HCOOH] 7 1.889 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.01; 3.04 (2s,6H, 2xCH₃); 7.72; 8.01; 8.57; 8.75; 9.34; 9.38; 9.41 (7H, ═CH,aryl/hetaryl). LC-MS = 268.0 (M + 1) [without HCOOH] 8 2.237¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.42 (s, 3H, CH₃; 8.65; 8.82; 9.33;9.43; 9.64 (5H, ═CH, aryl/hetaryl). LC-MS = 335.9 (M + 1) [withoutHCOOH] 9 3.125 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 1.16 (t, 3H, CH₃); 3.37(m, 2H, CH₂); 3.95 (s, 3H, CH₃); 3.57 (2s 6H, 2xCH₃); 8.17; 8.41; 8.54;9.11; 9.23 (5H, ═CH, aryl/ hetaryl). LC-MS = 271.1 (M + 1) [withoutHCOOH] 10 2.575 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 2.93 (s, 6H, 2xCH₃);8.62; 8.65; 8.82; 9.32; 9.42; 9.64 (6H, ═CH, aryl/hetaryl). LC-MS =365.1 (M + 1) [without HCOOH] 11 2.138 ¹H-NMR(400.0 MHz, d₆-DMSO): δ =3.32; 3.72 (2s 6H, 2xCH₃); 7.73; 8.10; 8.57; 9.46 (4H, ═CH,aryl/hetaryl). LC-MS = 284.1 (M + 1); 283.28 (calculated) 12 2.409¹H-NMR(400.0 MHz, d₆-DMSO): δ = 1.16 (t 3H, CH₃); 3.37 (m, 2H, CH₂);8.45; 8.61; 8.80; 9.31; 9.36; 9.55 (6H, ═CH, aryl/hetaryl). LC-MS =286.0 (M + 1) 285.27 (calculated) 13 2.592 ¹H-NMR(400.0 MHz, d₆-DMSO): δ= 0.71 (m 4H, CH₂CH₂); 8.51; 8.77; 8.88; 9.37; 9.55; 9.58 (6H, ═CH,aryl/hetaryl). LC-MS = 281.0 (M + 1) 280.28 (calculated) 14 1.963¹H-NMR(400.0 MHz, d₆-DMSO): δ = 2.86 (d, 3H, CH₃); 8.50; 8.77; 8.88;9.39; 9.56 (5H, ═CH, aryl/ hetaryl). LC-MS = 255.0 (M + 1) 254.24(calculated) 15 2.044 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.03 (d, 6H,2xCH₃); 8.02; 8.77; 8.88; 9.37; 9.48; 9.56 (6H, ═CH, aryl/hetaryl).LC-MS = 269.1 (M + 1) [without HCOOH] 16 1.960 ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 1.18 (t, 3H, CH₃); 3.37 (m, 2H, CH₂); 8.50; 8.77; 8.88;9.39; 9.56; (5H, ═CH, aryl/hetaryl). LC-MS = 269.0 (M + 1) 268.27(calculated) 17 2.602 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 1.20 (d, 6H,2xCH₃); 4.16 (m, 1H, CH); 8.60; 8.63; 8.80; 9.31; 9.37; 9.56 (7H, ═CH,aryl/hetaryl). LC-MS = 300.0 (M + 1); 299.30 (calculated) 18 2.567¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.95; 2.92 (2s, 6H, 2xCH₃); 8.20; 8.55;8.58; 9.22; 9.28 (5H, ═CH, aryl/ hetaryl). LC-MS = 350.1 (M + 1)[without HCOOH] 19 2.521 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 2.87 (d, 3H,CH₃); 8.45; 8.61; 8.80; 9.31; 9.36; 9.55 (6H, ═CH, aryl/ hetaryl). LC-MS= 271.9 (M⁺); 271.24 (calculated) 20 2.420 ¹H-NMR(400.0 MHz, d₆-DMSO): δ= 2.02 (d, 6H, 2xCH₃); 8.01; 8.61; 8.79; 9.31; 9.34; 9.48 (6H, ═CH,aryl/hetaryl). LC-MS = 285.9 (M⁺); 285.2763 (calculated) 21 2.099¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.32; 3.72 (2s, 6H, 2xCH₃); 8.10; 8.77;8.88; 9.39; 9.50, 9.56 (6H, ═CH, aryl/hetaryl). LC-MS = 285.1 (M + 1)[without HCOOH] 22 1.834 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.31; 3.71 (2s,6H, 2xCH₃); 8.11; 9.36; 9.51; 9.60 (4H, ═CH, aryl/ hetaryl). LC-MS =285.1 (M + 1); 284.27 (calculated) 23 2.104 ¹H-NMR(400.0 MHz, d₆-DMSO):δ = 2.99; 3.02 (2s, 6H, 2xCH₃); 7.94; 8.16; 8.54; 9.02; 9.29 (5H, ═CH,aryl/ hetaryl). LC-MS = 285.1 (M + 1) [without HCOOH] 24 2.251¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.40; 3.95 (2s, 6H, 2xCH₃); 8.20; 8.59;9.22; 9.29 (4H, ═CH, aryl/ hetaryl). LC-MS = 321.1 (M + 1) [withoutHCOOH] 25 2.376 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 1.64 (t, 3H, CH₃); 3.81(m, 2H, CH₂); 3.94 (s, 3H, CH₃); 8.18; 8.46; 8.56; 9.14; 9.26 (5H, ═CH,aryl/hetaryl); 8.92 (br., 1H, NH). LC-MS = 321.0 (M + 1); 320.29(calculated) 26 2.112 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.71; (s, 3H,CH₃); 8.08; 8.61; 8.79; 9.31; 9.35; 9.49 (6H, ═CH, aryl/ hetaryl). LC-MS= 302.0 (M + 1); 301.27 (calculated) 27 2.647 ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 1.65 (t, 3H, CH₃); 3.83 (m, 2H, CH₂); 8.51; 8.60; 8.80;9.31; 9.40; 9.58 (6H, ═CH, aryl/hetaryl); 8.96 (br, 1H, NH). LC-MS =336.0 (M + 1); 335.28 (calculated) 28 2.485 ¹H-NMR(400.0 MHz, d₆-DMSO):δ = 1.64 (s, 3H, CH₃); 3.83 (m, 2H, CH₂); 7.71; 8.51; 8.56;8.74; 9.38;9.53 (6H, ═CH, aryl/hetaryl); 8.95 (br., 1H, NH). LC-MS = 318.1 (M + 1)[without HCOOH] 29 1.888 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 0.71 (m, 4H,CH₂CH₂); 2.94 (m, 1H, CH); 7.71; 8.44; 8.55; 8.68; 8.74; 9.32; 9.37;9.50 (7H, ═CH, aryl/hetaryl + NH). LC-MS = 280.0 (M + 1); 279.29(calculated) 30 2.040 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 2.86 (d, 3H, CH₃);7.71; 8.44; 8.54; 8.75; 9.35; 9.37; 9.50 (7H, ═CH, aryl/hetaryl). LC-MS= 254.0 (M + 1) [without HCOOH] 31 2.629 ¹H-NMR(400.0 MHz, d₆-DMSO): δ =1.15 (t, 3H, CH₃); 3.36 (m, 2H, CH2); 7.71; 8.45; 8.56; 8.76; 8.80;9.37; 9.51 (7H, ═CH, aryl/hetaryl). LC-MS = 268.0 (M + 1); 267.28(calculated) 32 2.133 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.30; 3.71; 3.94(3s, 9H, 3xCH₃); 8.03; 8.17; 8.55; 9.06; 9.22 (5H, ═CH, aryl/hetaryl).LC-MS = 287.1 (M + 1) [without HCOOH] 33 2.182 ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 1.24 (d, 6H, 2xCH₃); 4.16 (m, 1H, CH); 8.17; 8.40; 8.54;9.12; 9.22 (5H, ═CH, aryl/hetaryl). 34 2.167 ¹H-NMR(400.0 MHz, d₆-DMSO):δ = 3.75 (br, 2H, CH₂); 6.17 (dt, 1H, CH); 8.17; 8.45; 8.55; 9.14; 9.25(5H, ═CH, aryl/hetaryl); 9.02 (br., 1H, NH). LC-MS = 307.1 (M + 1)[without HCOOH] 35 1.840 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 2.84 (d, 3H,CH₃); 3.94 (s, 3H, CH3); 8.16; 8.40; 8.54; 9.11; 9.22 (5H, ═CH,aryl/hetaryl), 8.72 (1H, NH). LC-MS = 257.0 (M + 1) [without HCOOH] 363.085 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 3.76 (m, 2H, CH₂); 6.18 (dt, 1H,CH); 7.71; 8.50; 8.56; 8.75; 9.05; 9.38; 9.53 (7H, ═CH, aryl/hetaryl).LC-MS = 304.1 (M + 1); 303.26 (calculated) 37 2.469 ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 0.70 (m, 4H, CH₂CH₃); 2.92 (m, 1H, CH); 8.16; 8.40; 8.54;9.11; 9.19 (5H, ═CH, aryl/hetaryl), 8.63 (1H, NH). LC-MS = 283.1 (M + 1)[without HCOOH] 38 2.792 ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 1.21; 1.23 (2s,6H, 2xCH₃); 4.15 (m, 1H, CH); 7.71; 8.44; 8.55; 8.74; 9.36; 9.38; 9.51(7H, ═CH, aryl/hetaryl). LC-MS = 282.1 (M + 1); 281.31 (calculated)

BIOLOGICAL EXAMPLES

Myzus Persicae—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the formulation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 500 g/ha:1, 4, 6, 7, 8, 10.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 90% at an application rate of 500 g/ha:3, 5, 11, 14, 15, 19, 20, 26, 28, 29, 30, 31, 36.

Tetranychus Urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the specified parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the formulation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 90% at an application rate of 500 g/ha:3.

Musca Domestica Test

Solvent: dimethyl sulfoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulfoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activecompound formulation of the desired concentration are populated with 10adult houseflies (Musca domestica).

After 2 days, the kill in % is determined. 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds of the preparationexamples showed an efficacy of 80% at an application rate of 100 ppm:14, 15.

1. The compound of the formula (I)

in which A represents an A radical from the group consisting of (A-a) to(A-f)

where the broken line represents the bond to the nitrogen atom of thebicyclic system of the formula (I) and G¹ represents N or C—B¹, B¹represents a radical from the group consisting of hydrogen, halogen,cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each caseoptionally substituted cycloalkyl and cycloalkenyl, B² represents aradical from the group consisting of hydrogen, halogen, cyano, nitro,alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionallysubstituted cycloalkyl and cycloalkenyl, T represents oxygen or anelectron pair, R² a) represents a radical from the group consisting of(B-1) to (B-36)

where the broken line denotes the bond to the carbon atom of thebicyclic system of the formula (I), or R² b) represents a D radical fromthe group consisting of (D-1) to (D-3)

where the broken line denotes the bond to the carbon atom of thebicyclic system of the formula (I), or R² c) represents a radical of theformula

where the broken line denotes the bond to the carbon atom of thebicyclic system of the formula (I), or R² d) represents a radical of theformula

where the broken line denotes the bond to the carbon atom of thebicyclic system of the formula (I), or R² e) represents an F radicalfrom the group consisting of (F-1) to (F-11)

where the broken line denotes the bond to the carbon atom of thebicyclic system of the formula (I), or R² f) represents a radical fromthe group consisting of haloalkyl, carboxyl and amino, in which G²represents hydrogen or a radical from the group consisting of halogen,nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl,haloalkyl, alkoxycarbonylalkyl, saturated or unsaturated cycloalkylwhich is optionally substituted and optionally interrupted by one ormore heteroatoms, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl,halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl,alkylsulfonylalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl,alkoxy(alkylsulfanyl)alkyl, alkoxy (alkyl sulfinyl)alkyl, alkoxy (alkylsulfonyl)alkyl, bi s (alkyl sulfanyl)alkyl, bis(haloalkylsulfanyl)alkyl,bis(hydroxyalkylsulfanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl,alpha-hydroxyiminoalkoxycarbonylalkyl,alpha-alkoxyiminoalkoxycarbonylalkyl, C(X²)NR³R⁴, NR⁶R⁷, alkylthio,alkylsulfinyl, alkylsulfonyl, the heterocyclyl radicals dioxanyl,dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl,oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl,dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide,oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide,oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl,oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl,dihydrooxazinyl and pyrazolinonyl (which for their part may besubstituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (whichfor its part may be substituted by halogen, cyano, nitro, alkyl andhaloalkyl), the heteroaryl radicals pyridyl, pyridyl N-oxide, pyrimidyl,imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl,tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyland isoquinolinyl (which for their part may be substituted by halogen,nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio,alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicalstriazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (whichfor their part may be substituted by halogen and alkyl), or G²represents a C radical from the group consisting of (C-1) to (C-9)

where the broken line denotes the bond to the radicals (B-1) to (B-36),X represents oxygen or sulfur, X¹ represents a radical from the groupconsisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,cycloalkyl, alkoxy and haloalkoxy, X² represents oxygen, sulfur, NR⁵ orNOH, L represents oxygen or sulfur, V-Z represents R²⁴CH—CHR²⁵ orR²⁴C═CR²⁵, n represents 1 or 2, m represents 1, 2, 3 or 4, R representsNR¹⁸R¹⁹, or represents an in each case optionally substituted radicalfrom the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl,alkyl-S-alkyl, alkyl-S(O)-alkyl, alkyl-S(O)₂-alkyl, R¹⁸—CO-alkyl,NR¹⁸R¹⁹—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl,hetaryl and hetarylalkyl, R³ represents hydrogen or alkyl, R⁴ representsa radical from the group consisting of hydrogen, alkyl, haloalkyl,cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl,alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl,alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, R⁵ represents aradical from the group consisting of hydrogen, alkyl, haloalkyl,cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl,alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl andhetarylalkyl, or R³ and R⁴ together with the nitrogen atom to which theyare attached form a ring which may contain one or more furtherheteroatoms from the group consisting of nitrogen, oxygen and sulfur, orR³ and R⁵ together with the nitrogen atoms to which they are attachedform a ring, R⁶ represents hydrogen or alkyl, R⁷ represents a radicalfrom the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl,alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl,alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl,alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl,or R⁶ and R⁷ together with the nitrogen atom to which they are attachedform a ring which may contain one or more further heteroatoms from thegroup consisting of nitrogen, oxygen and sulfur, R⁸ represents a radicalfrom the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl,alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionallyhalogen-substituted alkylcarbonyl and alkylsulfonyl, optionallyhalogen-substituted alkoxycarbonyl, optionally halogen-, alkyl-,alkoxy-, haloalkyl- and cyano-substituted cycloalkylcarbonyl, or acation, or an optionally alkyl- or arylalkyl-substituted ammonium ion,R⁹ represents a radical from the group consisting of in each caseoptionally substituted alkyl, alkenyl and alkynyl, in each caseoptionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, inwhich the rings may contain at least one heteroatom from the groupconsisting of sulfur, oxygen (where oxygen atoms must not be directlyadjacent to one another) and nitrogen, in each case optionallysubstituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and anoptionally substituted amino group, R⁸ and R⁹ in the radicals (C-1) and(F-1), together with the N—S(O)n group to which they are attached, mayalso form a saturated or unsaturated and optionally substituted 4- to8-membered ring which may contain one or more further heteroatoms fromthe group consisting of sulfur, oxygen (where oxygen atoms must not bedirectly adjacent to one another) and nitrogen and/or at least onecarbonyl group, R¹⁰ represents hydrogen or alkyl, R⁸ and R¹⁰ in the(C-2) and (F-2) radicals, together with the nitrogen atoms to which theyare attached, may also represent a saturated or unsaturated andoptionally substituted 4- to 8-membered ring which may contain at leastone further heteroatom from the group consisting of sulfur, oxygen(where oxygen atoms must not be directly adjacent to one another) andnitrogen and/or at least one carbonyl group, R⁹ and R¹⁰ in the radicals(C-2) and (F-2), together with the N—S(O)n group to which they areattached, may also form a saturated or unsaturated and optionallysubstituted 4- to 8-membered ring which may contain one or more furtherheteroatoms from the group consisting of sulfur, oxygen (where oxygenatoms must not be directly adjacent to one another) and nitrogen and/orat least one carbonyl group, R¹¹ represents an in each case optionallysubstituted radical from the group consisting of alkyl, alkenyl,alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy,cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy,phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio,heteroarylalkoxy and heteroarylalkylthio, R¹² represents an in each caseoptionally substituted radical from the group consisting of alkyl,alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl,cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio,alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy,heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, R¹¹ and R¹² inthe radicals (C-3) and (F-3), together with the phosphorus atom to whichthey are attached, may also form a saturated or unsaturated andoptionally substituted 5- to 7-membered ring which may contain one ortwo heteroatoms from the group consisting of oxygen (where oxygen atomsmust not be directly adjacent to one another) and sulfur, R¹³ representsan in each case optionally substituted radical from the group consistingof alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R¹⁴ represents an ineach case optionally substituted radical from the group consisting ofalkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R¹⁵ represents aradical from the group consisting of in each case optionally substitutedalkyl, alkenyl and alkynyl, in each case optionally substitutedcycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings maycontain at least one heteroatom from the group consisting of sulfur,oxygen (where oxygen atoms must not be directly adjacent to one another)and nitrogen, in each case optionally substituted aryl, heteroaryl,arylalkyl and heteroarylalkyl and an optionally substituted amino group,R⁸ and R¹⁵ in the radicals (C-6) and (F-6), together with the N—S(O)ngroup to which they are attached, may also form a saturated orunsaturated and optionally substituted 4- to 8-membered ring which maycontain one or more further heteroatoms from the group consisting ofsulfur, oxygen (where oxygen atoms must not be directly adjacent to oneanother) and nitrogen and/or at least one carbonyl group, R¹⁶ representsa radical from the group consisting of hydrogen, in each case optionallysubstituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionallysubstituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which therings may contain at least one heteroatom from the group consisting ofsulfur, oxygen (where oxygen atoms must not be directly adjacent to oneanother) and nitrogen, in each case optionally substituted aryl,heteroaryl, arylalkyl and heteroarylalkyl and an optionally substitutedamino group, R⁸ and R¹⁶ in the radicals (C-7) and (F-7), together withthe nitrogen atom to which they are attached, may also form a saturatedor unsaturated and optionally substituted 4- to 8-membered ring whichmay contain one or more further heteroatoms from the group consisting ofsulfur, oxygen (where oxygen atoms must not be directly adjacent to oneanother) and nitrogen and/or at least one carbonyl group, R¹⁷ representsa radical from the group consisting of in each case optionallysubstituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionallysubstituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which therings may contain at least one heteroatom from the group consisting ofsulfur, oxygen (where oxygen atoms must not be directly adjacent to oneanother) and nitrogen, in each case optionally substituted aryl,heteroaryl, arylalkyl and heteroarylalkyl and an optionally substitutedamino group, R⁸ and R¹⁷ in the radicals (C-8) and (F-8), together withthe N—C(X) group to which they are attached, may also form a saturatedor unsaturated and optionally substituted 4- to 8-membered ring whichmay contain one or more further heteroatoms from the group consisting ofsulfur, oxygen (where oxygen atoms must not be directly adjacent to oneanother) and nitrogen and/or at least one carbonyl group, R¹⁸ representsa radical from the group consisting of hydrogen, hydroxy, in each caseoptionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl,alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl,alkenyl and alkynyl, in each case optionally substituted cycloalkyl,cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the ringsmay contain at least one heteroatom from the group consisting of sulfur,oxygen (where oxygen atoms must not be directly adjacent to one another)and nitrogen, in each case optionally substituted aryl, arylalkyl,heteroaryl and heteroarylalkyl and an optionally substituted aminogroup, R¹⁹ represents a radical from the group consisting of hydrogen,represents an alkali metal or alkaline earth metal ion or represents anammonium ion which is optionally mono- to tetrasubstituted byC₁-C₄-alkyl or represents an in each case optionally halogen- orcyano-substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl,alkylsulfinylalkyl, alkylsulfonylalkyl radical, Y¹ and Y² independentlyof one another represent C═O or S(O)₂, Y³ represents a radical from thegroup consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl,haloalkyl, alkoxy, haloalkoxy and NR²⁰R²¹, W represents a radical fromthe group consisting of O, S, SO and SO₂, R²² represents a radical fromthe group consisting of alkyl, optionally halogen-, carbamoyl-,thiocarbamoyl- or cyano-substituted cycloalkyl, haloalkyl, alkoxy,haloalkoxy, alkoxyalkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl,haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylthioalkyl,alkylsulfinylalkyl, alkylsulfonylalkyl, alkylthioalkyloxy,alkylsulfinylalkyloxy, alkylsulfonylalkyloxy, haloalkylthioalkyl,halogenalkylsulfinylalkyl, haloalkylsulfonylalkyl, alkylthioalkenyl,alkylsulfinylalkenyl, alkylsulfonylalkenyl, alkenylthioalkyl,alkenylsulfinylalkyl, alkenylsulfonylalkyl, alkylcarbonylalkyl,haloalkylcarbonylalkyl, alkoxyalkyl, haloalkoxyalkyl,alkoxycarbonylalkyl, haloalkoxycarbonylalkyl, alkylaminosulfonyl,di(alkylamino)sulfonyl, or, in the case R²=d), R²² also representsoptionally substituted aryl or represents a radical from the groupconsisting of E-1 to E-51

R²⁰ represents a radical from the group consisting of hydrogen, halogen,cyano, nitro, amino, hydroxy and in each case optionally substitutedalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy,alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy,alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy,alkoxycarbonyloxy, alkylsulfonyloxy, alkylamino, alkenylamino,alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio,alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl,alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl,alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino,alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino,alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl,aryloxy, heteroaryl and heteroaryloxy, where the substituents areindependently of one another selected from halogen, cyano, nitro,hydroxy, amino, alkyl and haloalkyl, R²¹ represents a radical from thegroup consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl,alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl,haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl,alkylsulfonyl and haloalkylsulfonyl, R²³ represents a radical from thegroup consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy,alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl and R²⁴represents hydrogen or an in each case optionally substituted radicalfrom the group consisting of alkyl, alkenyl, alkynyl, phenyl andphenylalkyl and R²⁵ represents hydrogen or an in each case optionallysubstituted radical from the group consisting of alkyl, alkenyl,alkynyl, phenyl and phenylalkyl, R²⁷ represents hydrogen or alkyl andR²⁶ represents a radical from the group consisting of hydrogen, alkyl,haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl,alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.2. The compound of the formula (I) as claimed in claim 1, in which Arepresents a radical from the group consisting of (A-a), (A-b) and (A-f)

where the broken line represents the bond to the nitrogen atom of thebicyclic system of the formula (I), G¹ represents N or C—B¹, B¹represents a radical from the group consisting of hydrogen and fluorine,B² represents hydrogen, T represents an electron pair, R² c) representsthe radical of the formula

where the broken line denotes the bond to the carbon atom of thebicyclic system of the formula (I), X represents oxygen, R³ representsC₁-C₄-alkyl, R²² represents a radical from the group consisting ofC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₄-alkylsulfonyl and di-(C₁-C₄-alkyl)-aminosulfonyl and R²³represents hydrogen or C₁-C₆-alkyl.
 3. The compound of the formula (I)as claimed in claim 1 in which A represents the radical (A-b).
 4. Thecompound of the formula (I) as claimed in claim 1 in which A representsthe radical (A-f).
 5. The compound of the formula (I) as claimed inclaim 1 in which A represents the radical (A-a).
 6. A compositioncomprising a content of at least one compound of the formula (I) asclaimed in claim 1 and one or more customary extenders and/orsurfactants.
 7. A product comprising one or more compounds of theformula (I) as claimed in claim 1 or a composition thereof forcontrolling pests.